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Über den Podcast
Entra Chat is a weekly podcast hosted by Merill Fernando and delivers practical insights for Microsoft administrators and security professionals through conversations with identity experts who've been in the trenches. Episodes feature seasoned Entra practitioners sharing real-world deployment experiences and Microsoft Entra team members who build the features you use daily. Get the inside track on best practices, implementation strategies, and upcoming capabilities directly from those who design and deploy Microsoft identity solutions. Join us for actionable takeaways you can apply immediately in your Microsoft 365, Azure, and Entra environments. --- Entra.Chat, its content and opinions are my (Merill Fernando) own and do not reflect the views of my employer (Microsoft). All postings are provided “AS IS” with no warranties and is not supported by the author. All trademarks and copyrights belong to their owners and are used for identification only.
Folgen 85
Which Passkey Should Your Users Get? The FIDO Alliance CTO on Passkeys and Post-Quantum Cryptography
Microsoft is moving millions of users off SMS and onto passkeys, and most admins now have to decide which kind of passkey each group of users should get. Nishant Kaushik, CTO of the FIDO Alliance, the industry …
Shownotes
Microsoft is moving millions of users off SMS and onto passkeys, and most admins now have to decide which kind of passkey each group of users should get. Nishant Kaushik, CTO of the FIDO Alliance, the industry body behind the passkey standards, explains the three flavours of workforce passkey, how to roll out hardware security keys without repeating the RSA token years, and why passkeys are your best route to the post-quantum cryptography deadlines.
Key takeaways
Pick the right passkey for each user
* Passkeys are about phishing, not passwords. The FIDO Alliance set out to build phishing-resistant authentication that ordinary users never have to understand: public-key cryptography with the key management hidden in a credential manager or a security key. Judge every method by that test. Stacking phishable factors, such as a password, an SMS code and a push approval, only gives an attacker several things to phish, and that is easy to automate.
* Know the three flavours. Synced passkeys live in a credential manager that backs them up and restores them when a phone is lost. Device-bound passkeys on a hardware security key never leave the key: lose it and it’s gone. In the middle sits the option most people miss, a device-bound passkey in a workforce credential manager such as Microsoft Authenticator, managed by the organisation and used as the one strong authenticator for single sign-on.
* Match the flavour to the risk, then run it like any IT project. Assess your users, segment them, apply the control that fits each segment’s risk, and plan the whole lifecycle: onboarding, use, monitoring, recovery, revocation and deprovisioning. Synced passkeys didn’t take security away from device-bound ones; they gave you another option for the users who need it.
* Check what Microsoft’s rollout has already done in your tenant. Since 1 September 2026, users enabled for SMS and voice have been enabled for passkeys and prompted to register them unless an admin opted out, ahead of Microsoft-provided SMS and voice MFA retiring on 1 February 2027 (1 July 2027 for Global Administrators and external users). Unless passkey profiles or attestation restrict them, those users can register synced passkeys. Before you push back, ask whether the new method is better than the SMS code it replaces. For almost every user, it is.
Roll out hardware keys with intention
* Buy certified keys and bind them to a verified person. Use FIDO Certified security keys that your identity provider accepts. The best authenticator in the world is worth little if you don’t know who you handed it to, so tie registration to strong identity verification of the user.
* Plan the backup and the replacement before you need them. A device-bound key that’s lost is lost. Decide whether each user gets a second key or a synced passkey used only for account recovery alongside another check, and write the process for replacing a lost or compromised key. You’ll reuse that process when post-quantum-ready keys arrive.
Get a head start on post-quantum cryptography
* Start the PQC work now. A cryptographically relevant quantum computer could break the classical public-key cryptography behind TLS certificates, PKI and today’s passkeys, and some post-quantum cryptography (PQC) mandates land by the end of 2030. There were no PQC-ready hardware security keys on the market when this was recorded, but passkeys can move to new algorithms through a key rotation or a key swap. You can’t make a password or any other phishable method PQC-proof. The organisations that have already deployed passkeys and rehearsed key replacement will make that switch as a routine change rather than a scramble.
Watch the full conversation for how the FIDO standards came together, the running “year of PKI” joke, why Nishant’s kids pasted their password-manager passwords into a Google Doc, and the HTTP-to-HTTPS moment he thinks passkeys can repeat.
The FIDO Alliance published its Passkey Index 2026 on 15 October 2026, ahead of Authenticate 2026 (19-21 October, Carlsbad, California). Across the consumer services in the index, passkeys were used in 36% of successful sign-ins, up from 26% in 2025, and passkey sign-ins succeeded 93% of the time against 78% for traditional MFA. Read it at fidoalliance.org/passkey-index-2026.
Subscribe with your favorite podcast player or watch on YouTube
About Nishant Kaushik
Nishant Kaushik is the Chief Technology Officer of the FIDO Alliance, the industry association behind the FIDO standards that power passkeys. He has spent more than 25 years in digital identity and security, including CTO roles at Uniken and SCUID, Chief Architect at Identropy and Lead Strategist for Identity Management at Oracle. He writes the Talking Identity blog, serves on the RSA Conference Program Committee and the Identiverse Content Advisory Board, and is based in New York.
Website - nishantkaushik.com
Blog - blog.talkingidentity.com
LinkedIn - https://www.linkedin.com/in/nishantkaushik
Bluesky - https://bsky.app/profile/nishantkaushik.com
Related Links
From the conversation:
* FIDO Alliance Passkey Index 2026, published 15 October 2026 (mentioned at 44:15) - https://fidoalliance.org/passkey-index-2026/
* Authenticate, the FIDO Alliance conference, held 19-21 October 2026 in Carlsbad, California (mentioned at 44:23) - authenticatecon.com
* Passkeys by default and the retirement of Microsoft-provided SMS and voice authentication (mentioned at 02:10) - https://learn.microsoft.com/entra/identity/authentication/concept-sms-voice-retirement
* SMS and voice retirement FAQ, including third-party telephony providers - https://learn.microsoft.com/entra/identity/authentication/concept-sms-voice-retirement-faq
* What is the FIDO Alliance? (mentioned at 02:52) - https://fidoalliance.org/overview/
* FIDO specifications: UAF, U2F, and FIDO2 with WebAuthn and CTAP (mentioned at 08:01) - https://fidoalliance.org/specifications/
* W3C Web Authentication (WebAuthn) (mentioned at 08:17) - https://www.w3.org/TR/webauthn/
* FIDO Certified Products directory (mentioned at 10:11 and 34:02) - https://fidoalliance.org/certification/fido-certified-products/
* ASD Essential Eight maturity model changes: phishing-resistant MFA at Maturity Level Two (mentioned at 12:31) - https://www.cyber.gov.au/business-government/asds-cyber-security-frameworks/essential-eight/essential-eight-maturity-model-changes
* Configure Essential Eight MFA with authentication strengths in Microsoft Entra - https://learn.microsoft.com/compliance/anz/e8-mfa-configure-authentication-strengths
* NIST SP 800-63B-4: Authenticator Assurance Levels (mentioned at 13:00) - https://pages.nist.gov/800-63-4/sp800-63b/aal
* UK NCSC: Passkeys are more secure than traditional ways to log in (mentioned at 13:25) - https://www.ncsc.gov.uk/blogs/passkeys-are-more-secure-than-traditional-ways-to-log-in
* Death and the Digital Estate Community Group, OpenID Foundation (mentioned at 24:55) - https://openid.net/cg/death-and-the-digital-estate/
* FIDO Alliance white paper: Addressing FIDO Alliance’s Technologies in a Post Quantum World (mentioned at 32:32) - https://fidoalliance.org/white-paper-addressing-fido-alliances-technologies-in-post-quantum-world/
* NIST IR 8547: Transition to Post-Quantum Cryptography Standards (mentioned at 37:58) - https://csrc.nist.gov/pubs/ir/8547/final
Passkeys in Microsoft Entra ID:
* Enable passkeys (FIDO2) and passkey profiles (mentioned at 16:02) - https://learn.microsoft.com/entra/identity/authentication/how-to-authentication-passkeys-fido2
* Enable synced passkeys in Microsoft Entra ID - https://learn.microsoft.com/entra/identity/authentication/how-to-synced-passkeys
* Enable passkeys in Microsoft Authenticator (mentioned at 17:46) - https://learn.microsoft.com/entra/identity/authentication/how-to-enable-authenticator-passkey
* Temporarily opt out of the automatic passkey enablement (mentioned at 27:55) - https://learn.microsoft.com/entra/identity/authentication/concept-sms-voice-retirement#temporarily-opt-out-of-the-automatic-passkey-enablement
* Cond…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeFree AI Agents, the E7 Bill and AD vs Entra: The Workplace Ninjas US Special
AI agents are arriving in every Microsoft 365 tenant, and the questions admins ask first are what they cost to run and what it costs to secure them. In this Workplace Ninjas US special, four of the event’s …
Shownotes
AI agents are arriving in every Microsoft 365 tenant, and the questions admins ask first are what they cost to run and what it costs to secure them. In this Workplace Ninjas US special, four of the event’s speakers answer from the field: Jon Towles, founder of Workplace Ninjas US, Intune and AI tool builder Ugur Koc, Microsoft 365 security MVP Ru Campbell, and Spencer Alessi, the pen tester who defends Active Directory against Merill in the event’s AD vs Entra cage match.
Key takeaways
AI agents: cheap to run, not free to secure
* Admin agents can run on a laptop. You don’t need Security Compute Units, an E7 licence and Agent 365 just to query Microsoft Graph and reason over the results. Ugur’s answer is a local model that runs on a device with 8 GB of memory. His open-source OpenAdminOS runs agents as readable YAML files, top to bottom, through an MCP server and a local model such as Qwen on Ollama. “You don’t need like 10 SCUs to query your defender portal.”
* Review the tools you vibe-code before you share them. Ugur ran an agent-led security review over the new community projects for AwesomeIntune, found enough issues that he sent the authors fixes, and only published once they were merged. Keep API keys and secrets out of your repos, and treat every MCP connection as something to secure.
* An agent identity is free; securing it isn’t. Microsoft Entra Agent ID, with agent identities and blueprints, is available to every Entra customer. Conditional Access for agents needs Microsoft 365 E7, or Microsoft Agent 365 with at least Entra ID P1 or Microsoft 365 E3. Jon’s warning from the field: when the people using an agent don’t have Agent 365, “it’ll bypass conditional access when it talks to things like graph”. Budget for the licence before the agents go live.
Fix the baseline with one policy
* Block everything that isn’t on a managed device. Ru’s opening move when he hardens a new tenant: one Conditional Access policy for all users and all resources that requires a device marked as compliant or Microsoft Entra hybrid joined. “That’s the cheat code to securing Microsoft 365.” Start it in report-only and exclude your break-glass accounts.
* Know what each licence adds. Entra ID Free gives you security defaults. Entra ID P1, included in Business Premium, adds Conditional Access and the cheat code. E5 adds risk-based policies with P2. E7 matters once you add agents, because it includes Agent 365.
Cloud-native devices aren’t cloud-native identity
* Treat devices and identity as two decisions. Entra joined, Intune-managed devices work with users synced from Active Directory and can still reach file shares and Kerberos apps on-premises. Going cloud-only for identity is a separate, bigger step, and it’s the question behind the AD vs Entra debate.
* While AD is still there, keep defending it. Spence, a pen tester who talks mostly about Active Directory, is a fan of Entra and works in it every day. Plenty of tenants will run both for years, so follow the people who know AD as well as the ones who know Entra.
Watch the full conversation for how a Twitter fight became a conference session, the AD vs Entra scorecard, why Jon gives everyone an open bar and a puppy kennel, the 5K for Parkinson’s research, and who will still be running when the apocalypse comes. Explicit language.
Workplace Ninjas US 2027 runs 11-13 January 2027 at The Scott Resort & Spa in Scottsdale, Arizona. Tickets: workplaceninjas.us.
Sponsored by:
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New! ENow App Governance Accelerator 4.0 introduces App Onboarding, helping teams:
* Accelerate app approvals with configurable, multistage workflows.
* Evaluate security risks more efficiently with integrated Microsoft Defender for Cloud Apps risk scores.
* Reduce manual work with centralized requests, reviews, and approvals.
* Improve transparency with a self-service portal for requesters to track status and decisions.
* Control app sprawl with an Internal App Catalog of approved applications.
Go beyond Microsoft’s consent and approval capabilities with customizable, structured application governance, from the initial request through ongoing oversight.
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See It In Action: Request a Demo
Subscribe with your favorite podcast player or watch on YouTube
About the guests
Jon Towles (”Mobile Jon”) is the founder of Workplace Ninjas US, an end-user computing practitioner with a long background in identity, and a Microsoft MVP.
→ mobile-jon.com | linkedin.com/in/jontowles
Ugur Koc builds free community tools for Microsoft Intune admins, including AwesomeIntune, IntuneBrew and IntuneAssignmentChecker, and is the creator of OpenAdminOS, an open-source desktop app for running local AI agents against Intune, Entra and Defender. He’s based in Hamburg, Germany.
→ ugurkoc.de | linkedin.com/in/ugurkocde
Ru Campbell is a Microsoft 365 security, compliance, identity and management expert and Microsoft MVP, based in Scotland. At Workplace Ninjas US he co-presents a Conditional Access session and hardens an out-of-the-box tenant live in 60 minutes.
→ campbell.scot | linkedin.com/in/rlcam
Spencer Alessi (”TechSpence”) is a Senior Penetration Tester at SecurIT360 and a Microsoft MVP (Security - Identity & Access). A recovering sysadmin turned pen tester, he writes and talks about Active Directory security and builds free tools such as ScriptSentry, ADeleginator and AppLocker Inspector.
→ spenceralessi.com | linkedin.com/in/spenceralessi
Related Links
From the conversation:
* Workplace Ninjas US 2027, 11-13 January 2027, Scottsdale, Arizona (mentioned at 02:58 and 24:41) - workplaceninjas.us
* Workplace Ninjas US agenda (Ru’s sessions and the AD vs Entra cage match; the agenda loads from the event platform) - https://workplaceninjas.us/agenda/
* AwesomeIntune: free Intune community tools (mentioned at 05:43) - awesomeintune.com
* OpenAdminOS: local-first AI agents for IT administration (mentioned at 07:03) - openadminos.com
* OpenAdminOS on GitHub - https://github.com/OpenAdminOS/OpenAdminOS
* Ollama: run models locally (mentioned at 07:12) - ollama.com
* Qwen models (mentioned at 07:13) - qwen.ai
* Spencer Alessi’s site and Ethical Threat Insights (mentioned at 16:39) - spenceralessi.com
AI agents and licensing:
* Microsoft Security Copilot Security Compute Units and capacity (mentioned at 09:09) - https://learn.microsoft.com/en-us/copilot/security/security-compute-units-capacity
* Conditional Access for agent identities, licensing requirements (mentioned at 09:39) - https://learn.microsoft.com/en-us/entra/identity/conditional-access/agent-id
* What are agent identities? Microsoft Entra Agent ID (mentioned at 10:08) - https://learn.microsoft.com/en-us/entra/agent-id/what-are-agent-identities
* Overview of Microsoft Agent 365 - https://learn.microsoft.com/en-us/microsoft-agent-365/overview
Conditional Access baseline:
* Require device compliance with Conditional Access (mentioned at 11:46) - https://learn.microsoft.com/en-us/entra/identity/conditional-access/policy-all-users-device-compliance
* Conditional Access: Grant controls - https://learn.microsoft.com/en-us/entra/identity/conditional-access/concept-conditional-access-grant
* Conditional Access policy templates - https://learn.microsoft.com/en-us/entra/identity/conditional-access/concept-conditional-access-policy-common
* Microsoft Entra licensing (mentioned at 11:58) - https://learn.microsoft.com/en-us/entra/fundamentals/licensing
* Security defaults in Microsoft Entra ID (mentioned at 12:25) - https://learn.microsoft.com/en-us/entra/fundamentals/security-defaults
Devices, identity and naming:
* Microsoft Entra joined vs hybrid joined in cloud-native endpoints (mentioned at 14:55) - https://learn.microsoft.com/en-us/intune/solutions/cloud-native-endpoints/entra-join-types
* How SSO to on-p…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeEntra Multi-Tenant App Mistakes Every SaaS Builder and Admin Should Know, with Kelvin Tegelaar
Most SaaS vendors connect to your tenant with one multitenant app and one credential, shared by every customer. Kelvin Tegelaar, founder of CyberDrain and creator of CIPP (used by well over 10,000 MSPs), sees …
Shownotes
Most SaaS vendors connect to your tenant with one multitenant app and one credential, shared by every customer. Kelvin Tegelaar, founder of CyberDrain and creator of CIPP (used by well over 10,000 MSPs), sees it from both sides, and his verdict is blunt: “This app is dangerous, period.”
Recorded on 14 October 2026, one day before the ConnectWise Cloud Backup app’s credential was used to sign in to customer tenants (173 confirmed by Huntress).
Key takeaways
The risk: one app, every tenant
* One app registration, a service principal in every tenant. The credentials sit on the vendor’s app registration, so one leaked secret or certificate works in every tenant that consented, with whatever application permissions you granted. For MSP tools, GDAP widens it to every customer behind the partner.
* You can’t put Conditional Access on a vendor’s app. Conditional Access for workload identities covers single-tenant apps only. Watch vendor apps’ sign-ins, ask vendors how they protect their credentials, and know where the Enabled for users to sign-in? switch is so you can disable an app fast.
Fix the credentials
* Retire client secrets; let certificates rotate themselves. Prefer managed identity or federation; otherwise use short-lived certificates. CIPP’s last 30 days and are replaced every two weeks with Microsoft Graph addKey/removeKey, not by granting the app Application.ReadWrite.All.
* Turn on app management policies. Block new client secrets and cap credential lifetimes. The tenant default policy is off until you enable it.
* Lock your app’s service principals. Builders: keep app instance property lock on (the default for new apps since June 2026), so customer tenants can’t add their own credentials to your app.
Fix the architecture
* Build one app per customer tenant. A leak in tenant A then stays in tenant A. It costs some engineering; one central app is “choosing convenience”, which is fine only if you choose it knowingly.
* Keep the apps you ship out of your corporate tenant. Separate tenants for corporate, Azure and the apps you publish, all secured to the same baseline. Decide early: an app registration can’t move between tenants.
Watch the full conversation for how Kelvin built CIPP out of spite, the vendor mistakes he sees most, and why a standard pen test won’t find any of this.
Sponsored by:
Know what’s in your tenant, and keep watching it
Every risk above lives in your own tenant: multitenant vendor apps with powerful permissions, client secrets and certificates that live for years, and app management policies nobody turned on. Maester, the free, open-source security test framework for Microsoft 365, finds them, with tests for long-lived app certificates, expiring credentials, privileged permissions nobody uses and app management restrictions.
Maester Cloud keeps watching after the first scan:
* Continuous monitoring: scheduled runs, each one diffed against the last, with drift alerts sent from your own Microsoft 365 mailbox.
* Assign each failed test to its owner and link a ticket.
* Track the work until it’s fixed: new failures, fixes since the last run and accepted risks, each pinned to a date and run ID.
* Every tenant in one place, switching between customers without signing in again. Unlimited users and tenants.
Self-hosted in your own Azure subscription for $99 a month or $1,188 a year, or through Azure Marketplace on your Azure invoice.
Subscribe with your favorite podcast player or watch on YouTube
About Kelvin Tegelaar
Kelvin Tegelaar is the founder of CyberDrain and the creator of CIPP, the CyberDrain Improved Partner Portal, an open-source, sponsor-funded tool that MSPs use to manage their customers’ Microsoft 365 tenants. He owns and is CTO of Lime Networks, an MSP in the Netherlands, and has been a Microsoft MVP for eight years. A system administrator rather than a developer by trade, he built CIPP in PowerShell and has blogged at CyberDrain.com for years about automating Microsoft 365 for MSPs.
GitHub - https://github.com/KelvinTegelaar
CyberDrain - cyberdrain.com
Related Links
From the conversation:
* Kelvin’s “accidental SaaS” blog post (mentioned at 02:25) - Referenced in the episode, but the blog post could not be found.
* Huntress: Never Just One Termite, 6 months of researching OAuth application attacks (rogue apps) (mentioned at 24:28) - https://www.huntress.com/blog/never-just-one-termite-6-months-of-researching-oauth-application-attacks
* Huntress: Traitorware, how hackers abuse legitimate apps to hijack Microsoft 365 - https://www.huntress.com/resources/traitorware-how-hackers-abuse-legitimate-apps-to-hijack-microsoft-365
* CIPP - cipp.app
* CIPP documentation - docs.cipp.app
* CIPP on GitHub - https://github.com/KelvinTegelaar/CIPP
* CyberDrain - cyberdrain.com
* Automating with PowerShell: making stolen tokens useless with Global Secure Access, by Kelvin Tegelaar - https://cyberdrain.com/automating-with-powershell-making-stolen-tokens-useless-with-global-secure-access/
* Huntress: vendor credential enables unauthorized access (the ConnectWise Cloud Backup incident) - https://www.huntress.com/blog/vendor-credential-enables-unauthorized-access
Multitenant apps and permissions:
* Application and service principal objects in Microsoft Entra ID (mentioned at 17:05) - https://learn.microsoft.com/en-us/entra/identity-platform/app-objects-and-service-principals
* allowedTenantsAudience (restrict a multitenant app to specific tenants, Graph beta) (mentioned at 17:18) - https://learn.microsoft.com/en-us/graph/api/resources/allowedtenantsaudience?view=graph-rest-beta
* How to configure app instance property lock (mentioned at 18:09) - https://learn.microsoft.com/en-us/entra/identity-platform/howto-configure-app-instance-property-locks
* Microsoft Graph permission types: delegated and application (mentioned at 18:48) - https://learn.microsoft.com/en-us/graph/permissions-overview
* Microsoft Graph permissions reference - https://learn.microsoft.com/en-us/graph/permissions-reference
* GDAP and the Secure Application Model (mentioned at 16:32) - https://learn.microsoft.com/en-us/partner-center/developer/gdap-and-secure-application-model
Credentials and rotation:
* Add and manage application credentials (mentioned at 21:00) - https://learn.microsoft.com/en-us/entra/identity-platform/how-to-add-credentials
* application: addKey (mentioned at 31:01) - https://learn.microsoft.com/en-us/graph/api/application-addkey?view=graph-rest-1.0
* Generate proof-of-possession tokens for rolling keys - https://learn.microsoft.com/en-us/graph/application-rollkey-prooftoken
* Configure app management policies (mentioned at 32:23) - https://learn.microsoft.com/en-us/entra/identity/enterprise-apps/configure-app-management-policies
* Managed identities and secretless authentication across tenants (mentioned at 28:21) - https://learn.microsoft.com/en-us/entra/identity/managed-identities-azure-resources/secretless-authentication
* Configure an app to trust a managed identity - https://learn.microsoft.com/en-us/entra/workload-id/workload-identity-federation-config-app-trust-managed-identity
Monitoring and response:
* Conditional Access for workload identities (mentioned at 27:38) - https://learn.microsoft.com/en-us/entra/identity/conditional-access/workload-identity
* Disable user sign-in for an application (mentioned at 26:26) - https://learn.microsoft.com/en-us/entra/identity/enterprise-apps/disable-user-sign-in-portal
Tenants:
* Secure Future Initiative: eliminate identity lateral movement (mentioned at 34:32) - https://learn.microsoft.com/en-us/security/zero-trust/sfi/eliminate-identity-lateral-movement
* Microsoft actions following attack by nation state actor Midnight Blizzard (mentioned at 34:32) - https://www.microsoft.com/en-us/msrc/blog/2024/01/microsoft-actions-following-attack-by-nation-state-actor-midnight-blizzard
* Workforce and external tenant configurations (Microsoft Entra External ID) (mentioned at 37:17) - https://learn.microsoft.com/en-us/entra/external-id/tenant-configurations
Related Entra.Chat Episodes
* Stolen Tokens, Agents and Universal CAE: What Global Secure …
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeConditional Access Gaps and the App Back Door, with Brandon Colley
Most Conditional Access gaps aren’t exotic. They come from reading policies the wrong way: as firewall rules with an “allow”, as a list of platforms that seems complete, as an MFA exception for the office that …
Shownotes
Most Conditional Access gaps aren’t exotic. They come from reading policies the wrong way: as firewall rules with an “allow”, as a list of platforms that seems complete, as an MFA exception for the office that made sense years ago. Brandon Colley has reviewed well over a thousand Conditional Access policies in customer assessments, and the same handful of mistakes come up in tenant after tenant.
Once those are fixed, the risk moves. Passkeys, privileged access and Conditional Access put more locks on the front door, the user sign-in. An app that was consented to years ago, holds a client secret and still has a stale redirect URI is a back door that none of those locks cover.
Brandon is a Senior Security Consultant at TrustedSec and a Microsoft Security MVP. He came from systems administration, learned Active Directory security at Trimarc, and now spends his days on cloud and on-premises assessments and the remediation that follows. These are the gaps he checks first, and the app and consent settings he has moved on to.
Security defaults can cover more admins than your policies
The free tier can be stricter than the paid one. Security defaults require MFA for 16 administrator roles. The Microsoft-managed policy “Multifactor authentication for admins accessing Microsoft Admin Portals”, and the “Require MFA for admins” template it mirrors, cover 14. The two extra roles in security defaults are Authentication Policy Administrator and Identity Governance Administrator.
If a small tenant is on security defaults, think hard before switching it off: the moment you do, you lose protections that you then have to rebuild in Conditional Access yourself.
Sponsored by:
ENow Software Introduces New Entra ID App Onboarding Experience
As user requests for SaaS and AI applications increase, Entra ID and M365 teams face a growing volume of security reviews, added hours of manual research, and bottlenecks.
New! ENow App Governance Accelerator 4.0 introduces App Onboarding, helping teams:
* Accelerate app approvals with configurable, multistage workflows.
* Evaluate security risks more efficiently with integrated Microsoft Defender for Cloud Apps risk scores.
* Reduce manual work with centralized requests, reviews, and approvals.
* Improve transparency with a self-service portal for requesters to track status and decisions.
* Control app sprawl with an Internal App Catalog of approved applications.
Go beyond Microsoft’s consent and approval capabilities with customizable, structured application governance, from the initial request through ongoing oversight.
Faster Approvals. Less Admin Work. Better Security Posture.
Learn More About ENow App Governance Accelerator 4.0
See It In Action: Request a Demo
Decide which roles are privileged yourself
“We require MFA on privileged roles” is easy to say in an audit. An assessment asks a harder question: privileged by whose definition? Brandon’s own list is about 36 roles, grouped into tier 0 and tier 1, the same tiering model Active Directory admins used 20 years ago.
Don’t lean on Microsoft’s mandatory MFA either. It covers the Azure portal, the Microsoft Entra admin center, the Intune admin center and the Microsoft 365 admin center, plus create, update and delete operations from Azure CLI, Azure PowerShell, the Azure mobile app and IaC tools. Microsoft Graph APIs are generally not in scope, so in some cases a single-factor sign-in can still reach Graph. Your Conditional Access still has to cover every app and every role you consider privileged.
Every platform is not all platforms
Conditions inside one policy combine with AND. A policy that requires MFA when the user is risky, the sign-in is risky and the location is outside the United States only fires when all three are true at once, so it almost never fires. Put conditions that should act on their own into separate policies.
The device platforms condition has the same trap. Ticking Android, iOS, Windows, macOS and Linux is not the same as “any device”. The platform comes from the user agent string, which isn’t verified and is easy to change, so a sign-in that claims an unknown platform matches none of your platform policies and walks past all of them. Microsoft’s recommended fix is a separate block policy: include Any device, exclude the platforms you support, and set the grant to Block access. Brandon covers how the spoofing works in his Petri article (linked below).
Watch this episode…
Conditional Access has no allow rule
Customers often ask for a policy that will “allow finance access to the finance app”. Conditional Access has no allow rule. A policy is an if-then statement: if the users, target resources and conditions match, then require MFA, a compliant device or another control, or block. Anything the policy doesn’t match passes through untouched.
So every time you narrow the users, the apps or the conditions to describe who should get in, you also shrink what the policy protects. Scope policies broadly and carve out exclusions on purpose.
Testing: ask what a policy doesn’t do
Testing usually covers the happy path: the right user opens the right app and gets an MFA prompt. The gaps are in the paths nobody tried: the user who isn’t in the group, the unmanaged device, the other network. Two locations, managed and unmanaged devices, a few apps and a few user types already make dozens of test cases, and every new condition (insider risk from Microsoft Purview, for example) multiplies them again.
The useful question isn’t “what does this policy do?” but “what doesn’t it do, and does something else cover that?” When you add a role or group to one policy, check whether it should come out of another.
Tools help:
* What If tool: simulate a sign-in for a user, app, device platform and location, and see which policies apply.
* Conditional Access Optimization Agent: Microsoft Security Copilot reviews your policies and suggests new policies (created in report-only mode) and changes for you to approve. It needs Microsoft Entra ID P1 and security compute units.
* AI with sanitized data: as a consultant, Brandon often can’t run tools inside a customer’s tenant. He exports the policies as JSON, removes tenant names, group names and IDs, and asks an AI model to explain a specific coverage question. Challenge the answers and verify them; don’t take them on trust.
User actions and device code flow
Two gaps Brandon still finds often:
* User actions. Conditional Access can target Register security information and Register or join devices. Without a policy on these, registering an MFA method or a device is protected only by whatever the sign-in itself required.
* Device code flow. Microsoft deploys a managed policy that blocks it in some tenants, but Brandon has seen it deployed only about three times. Check whether you need it: filter the sign-in logs by authentication protocol for device code and see who uses it. Legitimate users are usually input-constrained devices such as Teams phones and Teams Rooms. At one customer, the single device code sign-in turned out to be their own penetration test. Then block it with an authentication flows policy and exclude only what genuinely needs it.
Trusted locations: the exception that switches MFA off
A common policy reads: require strong authentication for all users, all apps, everywhere, except trusted locations. It was best practice once. In effect it means single-factor sign-in at the office, and it often survives after the rest of the policy has been modernized.
On Microsoft Entra joined and hybrid joined Windows devices you don’t need the exception for single sign-on. The primary refresh token (PRT) provides SSO to apps and carries the MFA claim. The exception only lets users skip strong authentication.
Flip how you use locations. Instead of using them to relax MFA, use them to lock down the accounts that can’t do MFA, such as service accounts, shared accounts and kiosk accounts, so they only work from specific IP ranges and devices.
While you’re there:
* MFA trusted IPs in the legacy MFA service settings ar…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeStop the Bleeding: Cleaning Up Apps, Secrets and Consent in Microsoft Entra
Most tenants have the same problem: hundreds of app registrations and service principals, client secrets that were set to expire in a hundred years, permission grants nobody remembers approving, and test …
Shownotes
Most tenants have the same problem: hundreds of app registrations and service principals, client secrets that were set to expire in a hundred years, permission grants nobody remembers approving, and test tenants that were never cleaned up. It’s tempting to start fixing the scariest app on the list. Jeff Sakowicz argues for a different order: stop the problem from growing first, then remove the debt that gives you the most risk reduction for the least disruption.
Jeff isn’t describing someone else’s product. He has spent most of his 14 years at Microsoft as a product leader on the Entra application platform, shaping the application and service principal model and the OAuth permissions and consent model that every Entra tenant runs on today. Publisher verification and risk-based step-up consent came out of that work, and he now leads part of the team building the platform behind Microsoft Entra Agent ID. Inside Microsoft, he’s the person teams call when an app incident needs untangling. This is his playbook for securing non-human identities, from client secret burndown and unused apps to consent phishing and the protections Microsoft runs in every tenant by default.
Prevention starts with policy
The best medicine is prevention. Before you clean anything up, go through the policy controls you already have and set them to block insecure configuration that doesn’t fit your organization’s risk tolerance. This is a balance, not a switch. “If you want the most secure system in the world, unplug the server, bury it underground. Your job is done.” Lock things down too hard and developers and end users will find other ways to get work done, especially now that they have agents to help them. Shadow IT is almost always less secure than what you stopped. So whenever a control blocks self-service, make sure people know what to do next and how to get unblocked quickly.
Treat high-value apps as production infrastructure
Microsoft runs customer-facing apps in tenants separate from its corporate tenant. Tenant-level isolation is a useful form of segmentation, and some large organizations do the same for their production assets. But a second tenant brings its own operational overhead, and a tenant that falls into chaos can leave you worse off than before.
Whatever you decide, treat your multitenant apps and high-value line-of-business apps as production infrastructure, the same way you would protect a database or a high-value Azure subscription. A good middle ground is to keep a close eye on the owners and sponsors of your high-value apps and agent identities. They are the people who can change those identities’ authentication configuration, so their accounts need good hygiene.
The easier win is test, demo and staging. If they still live in your productivity or production tenant, move them out. Midnight Blizzard showed how small dominoes lead to big consequences: Microsoft’s own write-up describes a password spray against a legacy, non-production test tenant account, followed by a legacy test OAuth application that had elevated access to the corporate environment.
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Many of the app and consent problems in this episode are exactly what Maester checks for: it runs security tests against your Microsoft Entra and Microsoft 365 configuration and tells you what passed and what failed.
Maester Cloud turns those results into a workflow your team can run every day:
* Assign an owner to each finding and link it to a ticket, instead of tracking remediation in a spreadsheet.
* See what got fixed since the last run, and record accepted risks.
* Catch drift with daily history and alerts when a setting changes.
* Every tenant in one place, without switching sign-ins.
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Map your surface area, then think in three dimensions
Before buying a new inventory tool, use the one you already have. If your organization already tracks production assets or other identities, bring your non-human identities into that system instead of running a parallel process. Then answer three questions: how many of these do I have, what categories of identity are in the portfolio, and what are the big categories of risk?
Jeff looks at risk in three dimensions:
* Active threats. Priority zero. Hand them to the SOC immediately.
* Posture. Surface area from misconfiguration, or configuration that was state of the art five years ago, such as the implicit flow for a single-page app. Weak credentials, insecure redirect URIs, unused identities and legacy protocols all live here.
* Blast radius. How much privilege each identity has, whether it’s used or not.
Most organizations end up with a huge list of high-privilege apps and posture issues. You will never get every risk to zero at that scale, so the job is to prioritise by risk and by return on effort.
Burn down secrets: stop the bleeding first
Say you’ve read the Solorigate reports and want to get client secrets off your non-human identities. Step one is to stop the bleeding: create an app management policy that blocks new password credentials from being added. App management policies can take an enforcement date, so only apps created after that date are affected and your hundreds of existing apps keep working while you fix them. There is no equivalent for user authentication methods.
Before you switch it on, find out how disruptive it will be. One new app a month that uses a password credential is easy to absorb. A hundred a day could grind the organization to a halt. Have the guidance and the exception process ready, and move the enforcement date if you need to.
Once the problem has stopped growing, turn to the debt. Split it into categories and start with the two ends of the spectrum:
* The most privileged. Apps with existing passwords that have app-only access to read all mailboxes or read and write all user profiles go to the top of the list. Move them to a stronger credential and check whether they need that access at all.
* The wholly unused. More on this below.
The end goal is system-managed credentials, using a managed identity or workload identity federation with a federated identity credential (FIC). You can argue a certificate’s private key is harder to leak than a secret, but as Jeff says, “a bad copy-paste is a bad copy-paste.” System-managed credentials also remove a big source of toil for developers, which helps when you need people to move.
Why mail is the flag
Mail permissions can look less frightening than broad directory permissions, but for many attacks mail is the goal. “Mail’s often the flag that the attacker’s trying to capture.” Other access is often just a way to move laterally or elevate privilege. Mail, Teams chats and files can be the end goal, and that is what most historical consent phishing attacks went after. A mailbox is also a good lateral movement tool: it can hold credentials and bank details, and it gives an attacker what they need to craft a convincing social engineering attack against everyone the victim emails or chats with every day.
Lost secrets make this worse. A secret that is valid for years, used by apps nobody can name, gives an attacker a way in without adding a new credential, so there’s no new event for you to trace.
Unused identities: the highest return on effort
A wholly unused identity is the highest-ROI bucket. “If you get rid of an unused identity, you might be knocking an item off of seven lists.” In one move you can remove a weak password, an insecure redirect URI, overprivileged access and some legacy protocol usage. Do your due diligence first, because some apps only run once a year at tax season. But removing something that is truly unused doesn’t disrupt anyone, and it can be done as a central action by a single team without engaging every app owner. That high-leverage central action is what Microsoft leaned into for its Secure Future Initiative work.
Then look at low-usage identities. They hide in plain sight: an identity with an automated runner that wakes up every day to run a test…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeStolen Tokens, Agents and Universal CAE: What Global Secure Access Adds to Entra ID
A phished and stolen refresh token is one of the most useful things an attacker can take from your tenant. It is a long-term artifact, which is why so many phishing attempts go after it. Alex Pavlovsky’s answer …
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A phished and stolen refresh token is one of the most useful things an attacker can take from your tenant. It is a long-term artifact, which is why so many phishing attempts go after it. Alex Pavlovsky’s answer to that attack is a feature every Entra ID P1 tenant already owns.
Compliant network is part of Global Secure Access, and, like source IP restoration, it comes with Entra ID P1. Put the GSA client on your devices, add one Conditional Access policy that blocks access from anywhere outside the All Compliant Network locations named location, and a stolen refresh token or PRT cookie no longer works from the attacker’s own machine. As Alex puts it, the token itself does not become bound, but your use of it is gated by being on your organization’s compliant network.
Merill is joined by two former colleagues who are Microsoft Entra PMs: Alexander (Alex) Pavlovsky from the Global Secure Access feature team, and Marilee Turscak, who works on helping customers adopt AI safely. They explain why Microsoft built networking into identity, walk through the compliant network policy and a BYOD sign-in with no client installed, and demo a network policy that stops an agent from deleting a file its user is allowed to delete.
Why a stolen token stops working
For phishing itself, Alex is clear that the main line of defence is still stronger credentials that do not involve passwords. Compliant network helps with what comes after: the newer attack patterns where refresh tokens are stolen and replayed.
If your tenant-wide policy says you can only authenticate from a compliant network, you can also only replay refresh tokens from a compliant network. PRTs become unusable unless they are used from a device that has GSA, which means your organization’s device. Alex says the same applies to ROADtools-style attacks with PRT cookies: none of that works with compliant network in place. The signal is also tenant-specific. A GSA device in tenant B satisfies compliant network in tenant B and nowhere else.
In the demo, Alex builds the policy in a few clicks: all users, all resources (so the primary refresh token, Entra ID itself and Microsoft Graph are covered), any network except compliant network locations, then block. Start it in report-only mode, watch who is not coming through compliant network, pilot with a smaller group and expand. You do not need the advanced GSA licences for this, but you do need the GSA client on your devices or a remote network sending the traffic.
And exclude your break glass accounts. Alex has taken many panicked customer calls from admins who forgot, and Marilee locked herself out of a test tenant this way recently.
One engine for identity and network
When Merill joined Microsoft, he couldn’t see why networking belonged to the identity team. Alex explains the reasoning. When identity picks up a signal that a user, session or token is at risk, the network has to hear about it quickly, and passing those signals between separate systems through traditional APIs is too slow at this scale. So Microsoft made the identity engine and the network engine one engine.
That design shows up in source IP restoration. Behind a typical proxy or security service edge, every user looks like they signed in from the provider’s shared IP range. GSA sends the user’s original source IP to Entra securely, so sign-in logs are accurate, Conditional Access can evaluate the user’s own IP, and Identity Protection’s location and impossible travel detections work again. It is also why compliant network works at all: the GSA edge shares a security engine with Entra ID, so it can tell Entra that this is a legitimate GSA device from a specific tenant, and Entra can trust that signal.
The network can tell agents from users
“Agents are super deterministic. They are very resourceful. They do not give up.” Alex also argues that saying no to agents means falling behind your competitors, so the question becomes how to protect their use.
GSA can detect when network access comes from an agent, and its policy rules can match on the HTTP method, the destination and whether a user or an agent is acting. Marilee’s baseline recommendation is to block sensitive actions by agents. In her demo, the Zava helper agent tries to remove a document from Dropbox and gets an “agent is not authorized” error, because a policy called “block agents from destructive actions” blocks the DELETE method for agents only. The user checkbox is left clear, so the person can still delete the file themselves. The logs show the same attribution, which Alex says is valuable even before you apply any policy.
Alex also describes Copilot Studio agents running through GSA with no client anywhere. A Copilot Studio admin checks one box to enable the GSA integration, and with Internet Access and a policy in place, that agent traffic flows through GSA and your policies apply.
BYOD without the client
Marilee shows a user on a personal device with no GSA client. When she signs in, she is prompted to switch to her work browser profile, and from then on Explicit Forward Proxy sends that profile’s traffic through GSA. When she tries to open Facebook, she is blocked inside the work profile and nowhere else on her device. Alex sees the managed Edge profile becoming a sandbox with secure network access and Purview DLP, which could reduce the need for remote browser isolation. The full client still gets the most features, including agent detection, and remote networks are a third way to send traffic through GSA.
Universal CAE now acts on device state
Continuous access evaluation used to depend on applications that understood it, which mostly meant SharePoint, Teams and Exchange. Send an app’s traffic through GSA and it becomes CAE-aware too, including private apps. If an admin is on an SSH session over GSA and Entra flags their identity, Alex says the session is dead within about two to five minutes, even if their token is good for another 90 minutes.
The week before recording, Microsoft added device state support. If Intune or a third-party MDM marks a device non-compliant in Entra ID, GSA asks the user to bring it back into compliance or lose network connectivity. User risk changes and device deletion or disablement also trigger it now. If you already run GSA, you get this without changing anything, which is Merill’s favourite kind of feature.
If you have Entra ID P1 and have never deployed the GSA client, compliant network is the place to start.
About Alexander Pavlovsky
Alexander Pavlovsky is a Product Manager on the Microsoft Entra Global Secure Access feature team. He has been at Microsoft for 22 years. He started in Microsoft Consulting, installing domain controllers and Exchange servers for customers from CDs, then moved to the identity product team as a customer-facing PM in the Entra GTP (Get To Production) team, later CXE (Customer Experience), helping organizations adopt Azure AD.
LinkedIn - https://linkedin.com/in/alexpav
About Marilee Turscak
Marilee Turscak is a Product Manager on the Microsoft Security team focusing on Microsoft Entra. For the past two years she has focused on getting customers deployed across the Microsoft Entra Suite, and she now works on helping customers adopt AI safely and securely.
LinkedIn - https://linkedin.com/in/marilee-turscak
Related Links
* What is Global Secure Access? - overview and the licensing table for each feature (mentioned at 10:08) - https://learn.microsoft.com/en-us/entra/global-secure-access/overview-what-is-global-secure-access
* Source IP restoration (mentioned at 15:07) - https://learn.microsoft.com/en-us/entra/global-secure-access/how-to-source-ip-restoration
* Universal Conditional Access (mentioned at 15:26) - https://learn.microsoft.com/en-us/entra/global-secure-access/concept-universal-conditional-access
* Universal Tenant Restrictions (mentioned at 15:26) - https://learn.microsoft.com/en-us/entra/global-secure-access/how-to-universal-tenant-restrictions
* Compliant network check with Conditional Access (mention…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeYour AI Coding Agent Is Creating Secrets You Don’t Know About
Ask a coding agent to build something that talks to another service and watch what it does. It creates a client secret. Then another one. As Arturo Lucatero puts it, next thing you know you have ten secrets …
Shownotes
Ask a coding agent to build something that talks to another service and watch what it does. It creates a client secret. Then another one. As Arturo Lucatero puts it, next thing you know you have ten secrets that were created without you knowing about it. At the speed AI is moving, he thinks we could be cleaning up a few million new secrets within six months.
That would undo a lot of hard work. Under Microsoft’s Secure Future Initiative, Microsoft spent years removing secrets from its own estate and helping customers do the same with managed identities and workload identity federation. The agent era is the window to make secretless the default before the habit sets in.
Arturo is a Principal Product Manager on Microsoft Entra Agent ID, and he helped launch Managed Service Identity, the feature we now call Managed Identities for Azure resources. In this episode he and Merill trace the whole path: why secrets break, how managed identity takes them away inside Azure, how workload identity federation extends that to AWS, GCP, Azure Arc and now AI vendors like Anthropic, and what that means for agents.
Secrets work until they don’t
A service principal with a client secret works. It works right up to the moment it gets leaked, expires in the middle of an important job, or turns out to have no clear owner, no rotation plan and no one who knows where it is stored. Managed identity moves that whole burden to the platform. The secret still exists, but the developer never sees it. The admin’s job shrinks to control-plane questions: which resource, which identity, and what it can access. Arturo also hints at what comes next: binding managed identity tokens to the resource so a leaked token is useless anywhere else.
Beyond Azure
Not every workload or data source lives in Azure. Workload identity federation lets a workload present a token from an identity provider you already trust, such as AWS, Google Cloud, GitHub or Kubernetes, and exchange it for an Entra token with no secret involved. Azure Arc brings managed identity to servers outside Azure, including the one under your desk, which raised a hard design question for the team: what happens to the secret when the machine is in someone’s basement?
Coding agents default to secrets
Coding agents learned from years of examples full of client secrets and Key Vault plumbing, so that is what they produce. Merill has to push his own agents back towards workload identity federation every time. Arturo hit the same problem from the inside: when he asked a coding agent to build with Agent ID, it created a plain service principal and named it “blueprint”. The fix was rewriting documentation and shipping agent skills that teach coding agents the right pattern.
Why agent identities still allow client secrets
Merill asks the obvious question. If secrets are this bad, why can an agent identity have one? Arturo’s answer is compatibility. Agent identities already authenticate through a federated identity credential flow under the hood, but many places that call agents cannot obtain an OIDC token yet. Without secrets or certificates as a fallback, people would simply keep using app registrations.
Open standards are the way out
Agents now cross identity providers and clouds every day. Entra is leaning on open standards so they can do that without secrets or interrupting users: SPIFFE identities that can be exchanged for Entra tokens, and ID-JAG, which lets admins pre-consent so an agent can reach a service like GitHub or Slack without prompting the user.
Arturo’s advice for anyone building today is simple: whatever you can do to avoid having a secret, do it.
Is Each App in Entra ID Still Worth Governing?
App registrations and enterprise applications accumulate. Owners change. Projects and pilots end. Credentials linger. And stale or unused apps and their permissions can continue adding risk and governance overhead long after their purpose is gone.
ENow App Governance Accelerator helps you understand and act on:
* What is in your Entra ID application estate
* Who owns business and technical decisions and management?
* Which apps, permissions, and credentials need attention?
* What can be safely cleaned up to reduce your attack surface on a continuous basis as your tenant grows and changes?
Get the visibility and automated workflows you need to investigate application lifecycles at scale, clear out stale apps, and stop wasting time governing applications that shouldn’t still be there in the first place.
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About Arturo Lucatero
Arturo Lucatero is a Principal Product Manager at Microsoft working on Microsoft Entra Agent ID, where he focuses on giving agents a strong, governable identity and on the developer experience for building with it, including skills that teach coding agents to use Agent ID correctly. He joined Microsoft’s identity team after a re-org moved him there from Power BI, worked on Connect Health, and then helped Stuart Kwan launch Managed Service Identity, now managed identities for Azure resources. Most of his career has been spent modernising non-human identities, from managed identity and Azure Arc to workload identity federation.
LinkedIn - https://www.linkedin.com/in/arturo-lucatero/
Related Links
* Microsoft Entra Agent ID skill for coding agents, in GitHub Copilot for Azure (mentioned at 32:52) - https://github.com/microsoft/GitHub-Copilot-for-Azure/blob/main/plugins/azure-skills/skills/entra-agent-id/SKILL.md
* AI-guided setup for Microsoft Entra Agent ID, using the skill with GitHub Copilot (mentioned at 32:52) - https://learn.microsoft.com/en-us/entra/agent-id/agent-id-ai-guided-setup
* Ben Reader: Access Azure Key Vault from a local Kubernetes cluster with Azure Arc workload identity (mentioned at 22:32) - https://powers-hell.com/2026/08/26/access-azure-key-vault-from-a-local-kubernetes-cluster-with-azure-arc-workload-identity
* Ben Reader: Run a PowerShell workload on a local Kubernetes cluster that talks to Microsoft Graph (mentioned at 22:32) - https://powers-hell.com/2026/09/08/run-a-powershell-workload-on-a-local-kubernetes-cluster-that-talks-to-microsoft-graph
* Managed identities for Azure resources, formerly Managed Service Identity (mentioned at 04:50) - https://learn.microsoft.com/en-us/entra/identity/managed-identities-azure-resources/overview
* Workload identity federation (mentioned at 15:18) - https://learn.microsoft.com/en-us/entra/workload-id/workload-identity-federation
* Workload Identity Federation for the Claude API (mentioned at 16:27) - https://platform.claude.com/docs/en/manage-claude/workload-identity-federation
* Agent identity blueprints in Microsoft Entra Agent ID (mentioned at 20:35) - https://learn.microsoft.com/en-us/entra/agent-id/agent-blueprint
* Access Azure resources with managed identity on Azure Arc-enabled servers (mentioned at 23:09) - https://learn.microsoft.com/en-us/azure/azure-arc/servers/managed-identity-authentication
* SPIFFE and SPIRE (mentioned at 27:41) - https://spiffe.io/
* Federate a SPIFFE/SPIRE workload identity with Microsoft Entra ID (mentioned at 29:25) - https://learn.microsoft.com/en-us/entra/workload-id/workload-identity-federation-spiffe-spire
* Pieter Kasselman: SPIFFE at the BotAuth BoF, IETF 123 (mentioned at 29:53) - https://datatracker.ietf.org/meeting/123/materials/slides-123-webbotauth-spiffe-at-the-botauth-bof-pieter-kasselman-00
* Identity Assertion JWT Authorization Grant (ID-JAG), IETF draft (mentioned at 30:21) - https://datatracker.ietf.org/doc/draft-ietf-oauth-identity-assertion-authz-grant/
* Microsoft Secure Future Initiative (mentioned at 06:30) - https://www.microsoft.com/en-us/trust-center/security/secure-future-initiative
Related Entra.Chat Episodes
* One Compromised Agent ID Blueprint Can Cross Tenant Boundaries - https://entra.news/p/one-compromised-agent-id-blueprint
* From Windows Core to Leading Agent ID: Vince Smith’s Microsoft Story - https://entra.news/p/from-windows-core-to-leading-agent
* Attackers Are Targeting the AI Ecosy…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeActive Directory Security Testing in Maester 2.2
Active Directory is not dead. It is nearly thirty years old, Microsoft is still shipping new capabilities and new telemetry for it, and most of the forests running today will outlive the people currently …
Shownotes
Active Directory is not dead. It is nearly thirty years old, Microsoft is still shipping new capabilities and new telemetry for it, and most of the forests running today will outlive the people currently administering them. What has changed is that you can now test it the same way you test your cloud tenant.
Maester, the open-source PowerShell testing framework, added Active Directory coverage: 269 opt-in checks across 19 areas, from users, groups, computers and service principal names through GPO state, DACLs, DNS, trusts, replication and schema. They run against your domain, not your tenant, and they are off unless you explicitly connect to Active Directory.
Mike Soule, who wrote and validated that test suite, and Sam Erde, Microsoft MVP and author of DLLPickle, join Merill at HIP Conf in Nashville to go through what the tests cover, how to run them safely, and where the project is heading.
Sponsored by:
Is Each App in Entra ID Still Worth Governing?
App registrations and enterprise applications accumulate. Owners change. Projects and pilots end. Credentials linger. And stale or unused apps and their permissions can continue adding risk and governance overhead long after their purpose is gone.
ENow App Governance Accelerator helps you understand what’s in your Entra ID application estate, who owns it, which apps, permissions, and credentials need attention, and what can safely be cleaned up to reduce your attack surface on a continuous basis as your tenant grows and changes.
Get the visibility and automated workflows you need to investigate application lifecycles at scale, clear out stale apps, and stop wasting time governing applications that shouldn’t still be there in the first place.
Operational health is not the same as a security finding
The design decision that makes these tests usable is the split between operational patterns and security controls. Six groups nested in a row is not a vulnerability. Nesting is an intentional, functional capability. It is also nearly impossible to reason about when you are trying to work out where a permission actually comes from, and that is how incidents happen.
So not every test is pass/fail. Some exist to be investigated and monitored, and Maester’s tagging lets you baseline them and watch whether an anti-pattern is spreading or receding over time. The underlying guidance is a blend: years of health checks across dozens of forests, community research from teams like Semperis and SpecterOps, and Microsoft’s own documentation — which, for a product people keep declaring dead, is currently some of the best documentation and logging Microsoft ships. The new NTLM auditing in Windows Server is the example: the who, the why and the where of every NTLM authentication, instead of replaying events and correlating them yourself.
Maester is not trying to replace the likes of PingCastle, Purple Knight or Locksmith. Those tools offer real value, and the conversation now is about bringing those perspectives into one central platform.
The permissions you actually need
Everything the AD tests do is read-only. A plain domain user gets a surprising amount, because a directory is built to be readable — you will simply get a subset of the tests. The full set needs tier-zero read access, because some tests reach objects in the configuration container. In a tiered environment, that means running as a tier-zero admin from a privileged admin workstation.
Interactively, there is nothing to set up beyond line of sight to a domain controller, the ActiveDirectory module and PowerShell. The AD tests are excluded by default and have to be requested by tag. For automation, run a local runner, or give a container runtime a path back to a domain controller. Today the tests run as the logged-in user’s domain credentials; alternate credentials and group managed service accounts are on the road map.
Tiering, ESAE and the enterprise access model
There are no explicit tiering tests yet, but they are coming now that Microsoft has published implementation guidance. The history is worth knowing. ESAE — the Enhanced Security Admin Environment, the red forest — solved a real problem: inside Active Directory, a domain admin is trusted implicitly, so the source of authority needs to sit somewhere that is not self-referential. A separate management forest achieves that, at a cost in operational complexity that most organisations could not sustain. Microsoft has since moved to the enterprise access model, and in practice most teams landed in the middle: tiering based on access control, with tier zero for core identity infrastructure, tier one for servers, databases and applications, and tier two for workstations and the workforce.
The advice is not all-or-nothing. Any amount of effort you put into tiering is a good investment. Where Maester helps is codifying Microsoft’s recommended implementation as tests you can actually check yourself against, including the DACL and inheritance anti-patterns that accumulate through ordinary operations.
What is coming next
The dependency on the ActiveDirectory PowerShell module is on its way out. Almost all of this work is LDAP-level, so a .NET-based approach covers the vast majority of tests with no module dependency — which opens up Linux, macOS and non-domain-joined machines. Multi-domain aggregation is in progress; today a run covers a single domain at a time. And Maester 3 is being planned around a new engine for the built-in tests, with multi-threading and parallel execution, licensing handled centrally instead of inside every test, and Pester retained for backward compatibility and custom tests.
Subscribe with your favorite podcast player or watch on YouTube
About Michael Soule
Mike Soule is a Maester co-maintainer and National Director of Enterprise Architecture at Sentinel Technologies, where he works with enterprise customers on identity, cloud and security. He wrote and validated the Active Directory test suite that shipped in Maester 2.2 — 269 opt-in checks across 19 areas — and has been the project’s leading test contributor since the night after Maester’s launch talk at the PowerShell Conference, when he turned up the next morning with roughly thirty CISA tests already written.
LinkedIn - https://www.linkedin.com/in/mikesoule/
GitHub - https://github.com/soulemike
About Sam Erde
Sam Erde is a Maester co-maintainer and a Microsoft MVP, working at Patriot Consulting. He has spent more than twenty years in PowerShell, Active Directory, Group Policy, Exchange and Microsoft 365, contributes to open-source defensive tooling including Locksmith, and wrote DLLPickle, the module that gets you out of assembly version conflicts when several Microsoft modules are loaded in one session.
LinkedIn - https://www.linkedin.com/in/samerde/
GitHub - https://github.com/SamErde
Related Links
* Maester - open-source PowerShell test automation for Microsoft 365, Entra and now Active Directory (mentioned at 00:21) - https://maester.dev
* Introducing Maester 2.2 - the release that added 269 opt-in Active Directory checks across 19 areas (mentioned at 04:50) - https://maester.dev/blog/maester-2-2/
* Active Directory security testing in Maester - what the tests cover and how to run them (mentioned at 04:50) - https://maester.dev/blog/active-directory-security-testing/
* Maester on GitHub - source, tests and contribution guide (mentioned at 03:44) - https://github.com/maester365/maester
* Locksmith - Jake Hildreth’s AD CS assessment and remediation tool (mentioned at 05:11) - https://github.com/jakehildreth/Locksmith
* NTLM auditing enhancements in Windows 11 24H2 and Windows Server 2025 (mentioned at 09:53) - https://support.microsoft.com/en-us/topic/overview-of-ntlm-auditing-enhancements-in-windows-11-version-24h2-and-windows-server-2025-b7ead732-6fc5-46a3-a943-27a4571d9e7b
* AD DS tier model for privileged access security (mentioned at 24:47) - https://learn.microsoft.com/en-us/windows-server/identity/ad-ds/tier-model
* Securing privileged access - the enterprise access model …
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeMicrosoft Security Architect: Active Directory Is 10x Harder to Defend Than Entra
At Black Hat USA 2026, Microsoft’s David Weston put three numbers on a slide that anyone still running domain controllers should sit with. The Microsoft Security Response Center went from 80 patches in February …
Shownotes
At Black Hat USA 2026, Microsoft’s David Weston put three numbers on a slide that anyone still running domain controllers should sit with. The Microsoft Security Response Center went from 80 patches in February to 1,142 at the July Patch Tuesday. The fastest observed breakout time dropped from 98 minutes to 27 seconds. And mean time-to-exploit flipped from 63 days after a patch shipped to seven days before the patch existed.
Tarek Dawoud, Lead Architect on the Technical Excellence Team in Microsoft Security, walks Merill through those slides and then draws the conclusion for identity teams in his own words: “Active Directory is like 10x harder to defend than Entra.” If you do not already have a plan to move off AD, he says, sit down and write one.
He also says how Microsoft handles this itself. Most of Microsoft’s own servers run in the cloud, its front ends run with no domain at all, and on-prem AD survives mainly as a dial-tone service: the thing they need to bring Azure up from scratch, and not much else.
Tarek is back on Entra.Chat, and he was privy to a small part of Project Glasswing, where Microsoft got early access to Anthropic’s Mythos-class models to find vulnerabilities in its own products before attackers could. The red-team community was cynical at the time; what Microsoft saw internally was, in his words, “very concerning. Those things were damn good.” From there he builds Weston’s argument: the whole security industry rests on an assumption of scarcity. Vulnerabilities are rare, exploits are expensive, and attackers have recognisable tactics, techniques and procedures. Patch-and-pray works when bugs arrive slowly. TTP-based detection works when a human crew reuses its playbook. When a risk is small, driving it smaller is worth the money; as Tarek puts it, “if something has a 95% possibility of happening, pushing it down to 80% doesn’t change anymore.” The Hugging Face intrusion (an OpenAI agent, and not a deliberate attack, as Merill is quick to note) showed what happens when the old assumptions fail: the agent landed on one server and looped, try an exploit, fail, write a new tool, try again, with no attempt to hide and no signature to match. Hugging Face survived by repeatedly tearing down and rebuilding core infrastructure. Tarek’s question for listeners: “Does your AD team have that skill?” Tearing down and rebuilding domain controllers, he notes, is not a thirty-minute operation.
Hence the pitch: “Where you don’t need to own infrastructure, you shouldn’t manage infrastructure.” Tarek is explicit that this is his read of the moment rather than a mandate, and that it does not apply everywhere. Disconnected environments, military and intelligence, some manufacturing and IoT, and shielded OT networks such as utilities and remote mine sites are carved out; nobody is going to win the argument to punch a hole in an isolated OT environment to reach Entra. But for the ordinary case, collaboration, email, SharePoint, file shares, and apps that already live in Azure or AWS or even on-premises, he calls running your own identity infrastructure a losing battle. The minimum step is a strategy memo for your board that says what you are facing and why identity infrastructure investment needs to shrink.
Merill raises the two objections he hears most. First: you are just trusting Microsoft, and Entra ID has bugs too. Tarek’s answer is about who is on the hook. Microsoft owns and patches the Entra infrastructure; the service deploys roughly every 10 business days and can push a critical hotfix worldwide within a day or two, across a fleet that was already more than 100,000 compute nodes five years ago. You still have to handle Entra bugs, but the work looks like a Conditional Access policy to block a risky flow such as device code flow, not patching every server yourself. One customer he worked with had about 12 people in IAM for more than 200,000 employees; Entra has over 2,000. Second: this is licensing revenue and cloud stickiness dressed up as security. Tarek does not pretend to know the CAL math. “Assuming good intentions,” he says, the case is defensibility: the ports, the legacy protocols, the sheer number of things to watch, and the amount of legacy that is indefensible. That is where the “10x” line comes from: an architect’s rough comparison, not a measurement.
The back half is the path, using the Road to the cloud model at aka.ms/ad2entra. Map yourself to one of five states first: cloud attached, hybrid, cloud-first, AD minimized, cloud only. Then the moves that matter most. Decide, as a business, to stop buying apps that only run on-prem and make OAuth or SAML support a checkbox in the security review, because you will never turn off AD while a single LDAP app remains. Move devices to cloud management and out of hybrid join. Do not extend your domain into the cloud to manage servers; every cloud can patch and maintain a server without one, Microsoft’s own front ends run with no domain, and a domain you rely on becomes an attack vector for every server that trusts it. At the AD-minimized stage, HR provisions to Entra first (cloud HR, or API-driven inbound provisioning if your HR system is on-prem or file-based) and only the subset of users who need a stubborn legacy app is brought down to AD. The order of operations is apps first, then users and groups, with the Zero Trust Workshop identity pillar as the tracker for every box.
Tarek is honest about what is not solved. Intune does not manage servers today (Azure Arc is one approach), and some on-prem cases, such as retail stores that need local servers to keep point of sale running when the internet drops, still need a domain controller. The identity data warehouse, the layer that normalises HR data before it reaches the directory, is something SailPoint does well and Entra “doesn’t quite do yet,” so expect that MIM, SailPoint or Saviynt-style layer to persist. And the last two Exchange servers: object-level Source of Authority transfer exists now, but the attribute-level transfer that would let you switch just the mail properties to cloud management is still in progress. Tarek has met maybe five customers at stage 5. He still closes with hope. If the last thing standing before your domain controller is those two Exchange servers, you have succeeded, and “as someone who owns identity infrastructure, you do have a path out. There are people who have no path out.”
If you still own domain controllers and there is no written plan to stop, this episode is the memo.
What you will learn
* Why the scarcity assumption behind patching and TTP-based detection is breaking, and what the numbers on Weston’s slides (80 to 1,142 patches, 27-second breakout, exploits seven days before the patch) mean for anyone who owns servers.
* What the Hugging Face intrusion showed about how an AI agent actually attacks, and the one question to ask your AD team.
* How Tarek answers “Entra ID has bugs too” and “this is just licensing,” and what your residual burden looks like on an IDaaS.
* The five states of the Road to the cloud model, and why mapping where you are comes before any migration work.
* Why you do not need a domain to manage servers in the cloud, and where a domain controller is still legitimately needed.
* What changes at the AD-minimized state: HR to Entra first, API-driven provisioning for non-cloud HR, and why an identity data warehouse still exists.
* What actually keeps the last two Exchange servers alive, and how object-level versus attribute-level Source of Authority changes that.
* Which legacy protocols are the real blockers (NTLM and LDAP) and the options on the table: App Proxy, Entra Domain Services, Universal Print.
* How to use the Zero Trust Workshop identity pillar to track every step and stop the on-prem estate from growing.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Tarek Dawoud
Tarek Dawoud is Lead Architect on the Technical Excellence Team in Microsoft Security, part of the Microsoft Securit…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeHow General Motors Moved 200,000 People to Passkeys
Microsoft starts making passkeys the default in Microsoft Entra ID on 1 September 2026, and retires Microsoft-provided SMS and voice MFA on 1 February 2027. Every organisation with a large, messy population now …
Shownotes
Microsoft starts making passkeys the default in Microsoft Entra ID on 1 September 2026, and retires Microsoft-provided SMS and voice MFA on 1 February 2027. Every organisation with a large, messy population now has to answer a question that has nothing to do with passkey technology itself: how do you move a hundred thousand real people - office workers, factory floors, call centres and guests - without locking someone out?
In this episode, Merill sits down with the person who has already done it. Andrew Cameron is a Distinguished Engineer for Identity and Cybersecurity at General Motors, and he has spent roughly 25 years there, long enough to have started on the employee portal as a web architect in 2000, and then helped build the identity function that now carries one of the world’s largest passwordless deployments.
The single biggest lever, Andrew says, was almost embarrassingly simple. GM treated Windows Hello as an optional convenience for years, then realised that an already-managed Windows device is a passkey. About 100,000 people were enabled through Windows Hello alone - no roaming key, no phone, no authenticator juggling. Platform SSO now extends the same idea to Mac through the secure enclave.
The sequence matters as much as the tools. Admin roles came first, required to carry a device-bound passkey with Azure PIM forcing the stronger method through activation. Then Conditional Access did the rollout: a small group of eager users, audit mode, and then add apps and expand outward. Andrew’s practical tip is to target the big, heavily used apps before chasing every user - it often gets you to 80% coverage faster.
Then the conversation turns to the corners most passkey explainers skip. Manufacturing workers who cannot use a phone and do not have a keyboard. Guest accounts - suppliers, dealerships and contractors - whose source tenant must also enable passkeys before the journey can complete. Call-centre users on unmanaged devices. And VDI, where certificate auth or Azure Virtual Desktop fills the gap.
Andrew also walks through the synced-versus-device-bound decision, and lands on the unglamorous first step of the whole thing: before you retire anything, know which authentication methods are actually in use.
If your plan for the SMS/voice deprecation is “we’ll deal with it in February,” consider this episode your head start.
What caught GM’s identity team by surprise
Andrew was candid about the corners that bit them - the ones most admins only discover after the weak method is already gone:
* SMS was the onboarding bootstrap. A new starter was never expected to have a passkey, so onboarding simply defaulted to an SMS code. Remove SMS and you have also removed the way people got in on day one. GM’s fix: issue a Temporary Access Pass (TAP) for onboarding, then register a strong method immediately.
* A new phone defaulted to SMS again. The “I just got a new phone” recovery path sent a code to the number by default. That whole flow had to be redesigned too, not just the sign-in policy.
* Guests were the hard problem. Several hundred thousand suppliers, dealerships and contractors can only finish a passkey sign-in if their own source tenant has also enabled passkeys. Enforce on your side and a guest can still get blocked upstream through no fault of yours.
* Factory floors have no phones and no keyboards. Manufacturing workers could not use a phone or type a password, so GM built custom non-password methods and used hardware keys for robots and other physical assets.
* Call-centre users are not on managed devices. Tens of thousands of users were remote or unmanaged, so GM folded device posture and network location into the risk evaluation.
* VDI was a fresh corner. Certificate auth and Azure Virtual Desktop SSO replaced SMS as the way into a virtual desktop.
* Hardware-key attestation had to be unwound. GM had registered AAGUIDs for hardware keys; when synced passkeys arrived, those old attestation requirements no longer applied and had to be revisited.
GM’s secrets: don’t repeat the mistakes
* Your managed device is already a passkey. The light-bulb moment was realising Windows Hello turns an already-managed Windows device into a passkey — no phone required. It became the fast path for roughly 100,000 people, and Platform SSO does the same on Mac.
* Privileged roles first, then everyone else. Admin roles carried device-bound passkeys, with Azure PIM forcing the stronger method through activation.
* Use Conditional Access as the rollout engine. Small pilot group → audit mode → add apps → expand. No big bang.
* Target the big apps, not every user. You reach ~80% coverage faster by protecting the heavily used apps first, then adding more to the same policy.
* Know your authentication methods before you retire anything. Monitoring and visibility come first — the deprecation clock is not the plan.
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About Andrew Cameron
Andrew Cameron is a Distinguished Engineer for Identity and Cybersecurity at General Motors. He joined GM in 2000 as a web architect working on the employee portal, then moved into directory services and helped stand up GM’s identity and access management team in 2004. He has spent the past quarter-century building and leading identity and security at one of the world’s largest manufacturers from early SAML and OpenID Connect standardisation and Azure AD adoption, to GM’s current passwordless rollout across roughly 200,000 people.
LinkedIn - https://www.linkedin.com/in/kandrewcameron/
Related Links
* Passkeys by default and retirement of Microsoft-provided SMS and voice authentication (mentioned at 13:23) - https://learn.microsoft.com/entra/identity/authentication/concept-sms-voice-retirement
* Passkeys (FIDO2) authentication in Microsoft Entra ID (context throughout) - https://learn.microsoft.com/entra/identity/authentication/concept-authentication-passkeys-fido2
* Synced passkeys, device-bound passkeys and passkey profiles (discussed at 33:57) - https://learn.microsoft.com/entra/identity/authentication/how-to-authentication-passkeys-fido2
* Deploy phishing-resistant passwordless authentication (context at 28:38) - https://learn.microsoft.com/entra/identity/authentication/how-to-deploy-phishing-resistant-passwordless-authentication
* Configure a Temporary Access Pass (discussed at 12:48 and 33:20) - https://learn.microsoft.com/entra/identity/authentication/howto-authentication-temporary-access-pass
* Windows Hello for Business (the fast path discussed at 09:32 and 26:24) - https://learn.microsoft.com/windows/security/identity-protection/hello-for-business/
* Configure Platform SSO for macOS devices (discussed at 27:23) - https://learn.microsoft.com/intune/device-configuration/settings-catalog/configure-platform-sso-macos
* Require device compliance with Conditional Access (unmanaged-device discussion at 41:35) - https://learn.microsoft.com/entra/identity/conditional-access/policy-all-users-device-compliance
Related Entra.Chat Episodes
* 5 Lessons from Rolling Out Passkeys to Millions of Users - https://entra.news/p/5-lessons-from-rolling-out-passkeys
* From SMS MFA to Passkeys: A Practical Microsoft Entra Migrat…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeMicrosoft Entra memberOf Retirement: What Admins Must Do
On 3 November 2026, the memberOf operator in Microsoft Entra dynamic membership groups stops working. Nothing errors. Nothing breaks loudly. Every dynamic group, dynamic administrative unit and entitlement …
Shownotes
On 3 November 2026, the memberOf operator in Microsoft Entra dynamic membership groups stops working. Nothing errors. Nothing breaks loudly. Every dynamic group, dynamic administrative unit and entitlement management auto-assignment policy that uses it simply freezes in its last known state the people who should be added are not added, and the people who should be removed stay.
It was a preview feature for four years. It is in a lot of production tenants.
In this episode of Entra.Chat, Merill is joined by three guests for the first time: Gregor Reimling, Chief Azure Technologist at adesso SE and Microsoft MVP for Azure and Security; René Wasel, a Microsoft 365 specialist and Microsoft MVP; and returning guest Eric Woodruff, Chief Identity Architect at Semperis. Gregor and René co-organise the Cloud Identity Summit, which happens to fall on the same date the deprecation lands.
The conversation starts with the deadline and quickly becomes something more useful: an honest audit of what groups in Entra actually do, versus what administrators assume they do.
The memberOf operator existed because Entra does not resolve nested groups the way Active Directory does. It was a flattening trick — take the members of several groups and produce one flat group that applications, licensing and policies could read. With it going away, the panel walks through the realistic replacements: move to supported attribute-based rules where an attribute exists, stamp an attribute with PowerShell where one does not, or convert the group to assigned membership and script it. Gregor and René both raise the version of this that is easy to forget — a rule written years ago that nobody documented, using a sync rule editor nobody wants to reopen.
Then the discussion turns to the part that is not on any deprecation notice. Nested groups are supported in Conditional Access. They are not supported for group-based licensing, where only first-level members get a licence. They are not supported for Global Secure Access, where a nested group assigned to a traffic forwarding profile applies only to its direct members with no error, no warning, and nothing in the portal to tell you. Chris Brumm found that one and wrote a Maester test for it, because the only way to know is to go looking.
There is a new group property that blocks nesting in both directions, undocumented when this was recorded. Sensitivity labels have reached Entra security groups in preview, bringing a guest-access control that stops new guests but does not evict the ones already in the group. And Merill spotted something through Entra.News Daily that deserves more attention than it has had: an agent’s user account is a user identity, so existing dynamic user rules already evaluate it. If your licensing group has a broad rule and your developers start creating agent accounts, those accounts qualify. If it is a group behind a Conditional Access policy or an exclusion, that is a different conversation entirely.
Which leads to the sharpest point in the episode, and Eric makes it plainly: the security of a dynamic group is the security of the write permissions on the attributes in its rule. Some of those attributes are self-service. Some flow up from on-premises Active Directory, changed by people who are not thinking about the cloud at all. Microsoft Learn now carries an explicit warning about exactly this, and it is why groups used for privileged access cannot be dynamic.
The last third is about the Cloud Identity Summit itself. More info below.
If you have memberOf in a rule anywhere, the useful thing to do this week is find it. Everything else in this episode can wait until after November.
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Identity. Security. 2026. On Tuesday 3 November in Frankfurt, the Cloud Identity Summit gives cloud identity a conference of its own, now in its seventh year, and free to attend.
Two parallel tracks, Identity Management and Identity Security, run 50-minute sessions in English. It is deliberately vendor-neutral: Microsoft Entra, AWS, Google Cloud and whatever else you actually run. Eric Woodruff keynotes with Identity Security Kindergeburtstag fourteen years of identity being called “the new security perimeter”, and an honest look at what that has actually got us.
Why it is worth the trip:
* It is in person only. No livestream, no catch-up recordings. The organisers built it that way on purpose — “a strong focus on face-to-face conversations to support networking and exchange of experiences.” If you want the hallway conversation, you have to be in the hallway.
* Everything is identity. No filler tracks. A whole day of people who work on the same problems you do, from an international mix of industries.
* The Community Ticket is 100% free. There is an optional paid Supporter Ticket if you want to help fund the event.
* It is easy to get to. adesso SE, Prisma Frankfurt-Niederrad — around ten minutes by S-Bahn from Frankfurt Airport, ten from Frankfurt Hauptbahnhof, and a short walk from Frankfurt-Niederrad station.
* Travelling in? The Crowne Plaza Frankfurt is a ten-minute walk, €89 single with breakfast on the “Cloud Identity Summit” booking code — 50 rooms, held until 5 October.
One more thing, given what this episode is about: 3 November is also the day Microsoft retires the memberOf operator. If you are going to spend that Tuesday thinking about Entra groups anyway, spend it in a room with people solving the same problem.
Subscribe with your favorite podcast player or watch on YouTube
About Gregor Reimling
Gregor is a Microsoft MVP in Azure and Security, Chief Azure Technologist at adesso SE, and a passionate advocate for the Microsoft cloud community. His expertise spans Azure architecture, Microsoft Entra, Zero Trust and hybrid cloud environments; he helps organizations successfully navigate their cloud journey. Beyond his day job, Gregor is a frequent speaker at international events, co-host of the Cloud Inspires podcast and co-founder of the Cloud Identity Summit. As a Microsoft Certified Trainer, he enjoys sharing knowledge, mentoring others, and helping IT professionals get the most out of Microsoft technologies.
LinkedIn - https://www.linkedin.com/in/gregorreimling/
About René Wasel
René is a Microsoft 365 specialist, and a Microsoft MVP for Microsoft 365. He describes his work as helping people actually use the technology they have been given, and he is active in the community as a meetup and event organiser. He co-organises the Cloud Identity Summit.
LinkedIn - https://www.linkedin.com/in/renewasel/
About Eric Woodruff
Throughout his 25-year career in the IT field, Eric has sought out and held a diverse range of roles. Currently the Chief Identity Architect for Semperis; Eric previously was a member of the Security Research and Product teams. Prior to Semperis, Eric worked as a Security and Identity Architect at Microsoft partners, spent time working at Microsoft as a Sr. Premier Field Engineer, and spent almost 15 years in the public sector, with 10 of them as a technical manager.
LinkedIn - https://www.linkedin.com/in/ericonidentity/
Related Links
* MC1448379 - Microsoft Entra ID: Replace MemberOf rules by November 3, 2026 - https://mc.merill.net/message/MC1448379
* Entra.News Daily, Merill’s daily diff of Microsoft Entra documentation changes (mentioned at 26:26) - https://daily.entra.news/changes/2026-08-14/manage-rules-for-dynamic-membership-groups-in-microsoft-entra-id-16/
* Maester, the open-source test framework used for the dynamic-group and nested-group checks discussed (mentioned at 06:09 and 30:06) - https://maester.dev/contributors/agnivesh
* Configure dynamic membership groups with the memberOf operator - the official retirement notice and migration guidance - https://learn.microsoft.com/entra/identity/users/groups-dynamic-rule-member-of
* Manage rules for dynamic membership groups - covers agent user accounts and the attribute write-permission warning - https://learn.microsoft.com/entra/ide…
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribePass-the-Passkey: What Michael Grafnetter's Black Hat Research Means for Entra Admins
Passkeys are phishing-resistant. But that resistance is enforced by your browser, which binds every authentication to the origin that requested it. Skip the browser, and the guarantee weakens.In this episode of …
Shownotes
Passkeys are phishing-resistant. But that resistance is enforced by your browser, which binds every authentication to the origin that requested it. Skip the browser, and the guarantee weakens.
In this episode of Entra.Chat, I spoke with Michael Grafnetter, Principal Security Researcher at SpecterOps and Microsoft MVP, about the Pass-the-Passkey research he presented at Black Hat USA 2026. A family of attacks against passkey implementations across Windows, Microsoft Entra ID, browsers and password managers.
Michael starts with the vulnerability chain he reported to Microsoft. Windows was writing the complete passkey assertion into the event log, and Microsoft Entra ID would accept a replay of that assertion for up to ten minutes. Any user able to read those logs including a member of Remote Desktop Users on a shared server, or unprivileged malware quietly reading event logs without tripping EDR could impersonate whoever had just signed in. If that person was a Global Administrator, so was the attacker. Windows now truncates the logged message, and Microsoft Entra ID checks authenticator signature counters to reject replays.
One clarification Michael is emphatic about: private keys were never written to the event log. They stay bound to the TPM or never leave the security key at all. What leaked were the short-lived digital signatures made by those keys and for this attack, that was enough.
We also covered the attacks that do not depend on any single bug. Malware running without administrator rights can call the native Windows WebAuthn APIs directly and raise a passkey prompt flood that keeps returning until the user gives in and approves it. Synced passkeys, exported from a password manager and decrypted with a keylogged password, hand an attacker a credential with no ten-minute limit at all. And a browser-hooking technique Michael calls a passkey detour attack quietly redirects a legitimate assertion into the attacker’s own session.
The defensive thread running through all of it is the same: every one of these attacks assumes malware is already on the device. That makes device trust the key control. Privileged access workstations for administrators, Conditional Access requiring compliant devices with EDR running, and the clean source principle that says a system can only be as trustworthy as whatever it depends on.
Michael closes on an optimistic note, and it is worth repeating. Passkeys are still the future. They remain far better than passwords and phishable MFA, and every attack here costs an adversary vastly more effort than sending a phishing link. But as passkeys become the default in Microsoft Entra, the threat model deserves an honest read.
Watch the demos. This episode includes three on-screen demonstrations that are much easier to follow on video than on audio.
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About Michael Grafnetter
Michael Grafnetter is a Principal Security Researcher at SpecterOps and a Microsoft MVP, based in Prague. He specializes in Microsoft Entra ID and Active Directory security and PowerShell. He is the author of the DSInternals PowerShell module and the researcher who originally discovered the Shadow Credentials attack technique, now widely used by penetration testers, red teamers and attackers alike. He has presented his security research at international conferences including Black Hat Europe, Black Hat USA, SecTor, TROOPERS and BSides Lisbon.
* LinkedIn - https://www.linkedin.com/in/grafnetter/
Related Links
* Pass-the-Passkey research and tools, including Passkey Injector and the DSInternals.Passkeys module (discussed at 14:57 and 34:22) - https://github.com/SpecterOps/pass-the-passkey
* Pass-the-Passkey research paper from Black Hat USA 2026 (introduced at 07:34) - https://specterops.io/wp-content/uploads/sites/3/2026/08/Pass-the-Passkey_A4_v2.pdf
* Shadow Credentials, Michael’s earlier Active Directory research (mentioned at 01:46) - https://specterops.io/blog/2021/06/17/shadow-credentials-abusing-key-trust-account-mapping-for-account-takeover/
* DSInternals PowerShell module (mentioned at 01:34) - https://www.dsinternals.com/en/
* Passkeys (FIDO2) authentication in Microsoft Entra ID (context throughout) - https://learn.microsoft.com/entra/identity/authentication/concept-authentication-passkeys-fido2
* Synced passkeys, device-bound passkeys and passkey profiles (discussed at 23:21) - https://learn.microsoft.com/entra/identity/authentication/how-to-authentication-passkeys-fido2
* Deploy phishing-resistant passwordless authentication (context at 18:08) - https://learn.microsoft.com/entra/identity/authentication/how-to-deploy-phishing-resistant-passwordless-authentication
* Require device compliance with Conditional Access (recommended at 21:12) - https://learn.microsoft.com/entra/identity/conditional-access/policy-all-users-device-compliance
* Privileged access devices and the clean source principle (discussed at 21:55 and 35:41) - https://learn.microsoft.com/security/privileged-access-workstations/privileged-access-devices
* Unit 42, “Pass the Passkey: A Novel Attack Surface in Passwordless Authentication” — the Palo Alto research on Google Password Manager passkeys (mentioned at 26:27) - https://unit42.paloaltonetworks.com/passwordless-authentication-security-risks/
Related Entra.Chat Episodes
* From SMS MFA to Passkeys: A Practical Microsoft Entra Migration Plan - https://entra.news/p/from-sms-mfa-to-passkeys-a-practical
* 5 Lessons from Rolling Out Passkeys to Millions of Users - https://entra.news/p/5-lessons-from-rolling-out-passkeys
* Attackers Are Targeting The AI Ecosystem You Cannot See - https://entra.news/p/attackers-are-targeting-the-ai-ecosystem
Chapters
00:00 Intro
01:02 Meet Michael Grafnetter
03:09 How the Research Started
06:50 Windows Hello for Business Was the First Passkey
07:30 The Signature in Your Event Log
10:18 No, Private Keys Are Not Logged
12:25 How Entra Mitigated the Replay
13:44 Demo: Signing In With a Stolen Signature
15:22 Malware-Initiated Passkey Phishing
18:08 The Browser Is What Makes Passkeys Phishing-Resistant
20:42 What Defenders Should Actually Do
23:04 Synced Passkeys and the Export Problem
26:13 Credential Exchange and Password Manager Risk
28:19 The Passkey Detour Attack
30:43 The Authentication Broker Debate
31:57 RDP Redirection and Remote Passkey Abuse
32:59 Spotting a Suspicious Passkey Prompt
34:46 Passkeys Are Still the Future
Podcast Apps
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeFrom SMS MFA to Passkeys: A Practical Microsoft Entra Migration Plan
Microsoft-managed SMS and voice MFA will stop working on February 1, 2027. That deadline makes passkey planning urgent, but enabling a new authentication method is only the first milestone.In this episode of …
Shownotes
Microsoft-managed SMS and voice MFA will stop working on February 1, 2027. That deadline makes passkey planning urgent, but enabling a new authentication method is only the first milestone.
In this episode of Entra.Chat, Merill speaks with Jai Maharaj, Product Manager at Microsoft, about the practical journey from legacy MFA to a passwordless Microsoft Entra environment. Jai explains what is actually being retired, why organizations can still use a customer-managed telecom provider, and how passkey profiles support synced and device-bound passkeys for different user personas.
The user-experience case is compelling: Microsoft reports roughly 69 seconds for password plus traditional MFA compared with about three seconds for a synced passkey. The security case is stronger still. Passkeys resist phishing by design, but Jai stresses that deploying them does not make an organization phishing-resistant until it enforces the right authentication strength and addresses the passwords and legacy applications still in the environment.
The conversation then follows the complete identity lifecycle. How do you ensure the right person receives a passkey during onboarding? How do you verify someone requesting a sensitive role? How do you recover an account without relying on knowledge-based help-desk questions? Jai connects those scenarios to Microsoft Entra Verified ID, verifiable credentials, Face Check, identity verification partners, and self-service account recovery.
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About Jai Maharaj
Jai Maharaj is a Senior Product Manager at Microsoft. He works with customers and engineering teams across Microsoft Entra, with experience spanning ID Governance, Verified ID, External ID, and passkeys. He helps enterprise and public-sector organizations move from legacy authentication methods to phishing-resistant authentication.
* LinkedIn - https://www.linkedin.com/in/jai-maharaj-0938305a/
Related Links
* Microsoft-managed SMS and voice retirement timeline (discussed at 02:19 and 06:31) - https://learn.microsoft.com/entra/identity/authentication/concept-sms-voice-retirement
* Customer-managed telecom provider FAQ (mentioned at 03:41 and 07:13) - https://learn.microsoft.com/entra/identity/authentication/phone-providers-faq
* Passkey profiles, synced passkeys, and device-bound passkeys (discussed at 09:44) - https://learn.microsoft.com/entra/identity/authentication/how-to-authentication-passkeys-fido2#passkey-profiles
* Passkey concepts and Microsoft performance figures (mentioned at 14:22) - https://learn.microsoft.com/entra/identity/authentication/concept-authentication-passkeys-fido2#what-are-passkeys
* Microsoft Entra Verified ID Face Check (introduced at 31:57) - https://learn.microsoft.com/entra/verified-id/using-facecheck
* ASD/ACSC Essential Eight maturity model (mentioned at 33:41) - https://www.cyber.gov.au/business-government/asds-cyber-security-frameworks/essential-eight/essential-eight-maturity-model
* Microsoft Entra account recovery overview (discussed at 36:59) - https://learn.microsoft.com/entra/identity/authentication/concept-account-recovery-overview
* Verified ID identity verification partners (discussed at 37:12) - https://learn.microsoft.com/entra/verified-id/idv-partners
* Microsoft Entra licensing (discussed at 39:27) - https://learn.microsoft.com/entra/fundamentals/licensing
* Verified ID and Face Check pricing model (discussed at 39:27) - https://learn.microsoft.com/entra/verified-id/verified-id-pricing
* Deploy phishing-resistant passwordless authentication (mentioned at 52:34) - https://learn.microsoft.com/entra/identity/authentication/how-to-deploy-phishing-resistant-passwordless-authentication
Related Entra.Chat Episodes
* Microsoft Is Auto-Enabling Passkeys in March 2026 - https://entra.news/p/microsoft-is-auto-enabling-passkeys
* Mastering Microsoft Entra ID: Real-World Passkey Deployment Tips - https://entra.news/p/mastering-microsoft-entra-id-real
* Entra Ignite Recap: Synced Passkeys, Agent ID & The Future of Identity - https://entra.news/p/entra-ignite-recap-synced-passkeys
Chapters
00:00 Intro
02:19 Why Microsoft Is Retiring Managed SMS and Voice
03:32 What the February 2027 Deadline Means
09:27 Synced vs Device-Bound Passkeys
14:22 From 69 Seconds to Three
19:02 Making Passkeys Easier for Users
23:14 Customer Passkey Deployment Lessons
28:41 The Secure Bootstrapping Problem
31:57 Verified ID and Face Check
33:41 Essential Eight and High-Value Access
36:24 Self-Service Account Recovery
39:27 Licensing and Recovery Economics
44:45 Why Face Check Augments Passkeys
49:40 Enforce Phishing Resistance and Build a Roadmap
Podcast Apps
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeThe Ultimate Microsoft Entra Global Secure Access Migration Guide
An Entra GSA migration should not mean throwing away years of useful SSE policy work and rebuilding every application, segment, and rule by hand.Existing configuration carries hard-won intent: which populations …
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An Entra GSA migration should not mean throwing away years of useful SSE policy work and rebuilding every application, segment, and rule by hand.
Existing configuration carries hard-won intent: which populations need access, which destinations should be blocked, and which exceptions keep the business running. Migrate2GSA creates a path to preserve the useful parts while making the migration a deliberate cleanup opportunity.
In this episode of Entra.Chat, I spoke with Andres Canello, Principal Product Manager at Microsoft and creator of Migrate2GSA. Andres demonstrates how the open-source toolkit exports configuration from third-party products, converts it into a common CSV schema, gives administrators an intentional review step, and provisions the approved configuration into Global Secure Access through Microsoft Graph.
The goal is not to configure the product end to end or remove human judgment. Andres describes it as a way to accelerate the repetitive 80%. Conflicting segments default to “do not provision,” existing applications are skipped, generated Conditional Access policies remain disabled, and there is no delete API call in the toolkit.
The conversation also covers greenfield provisioning, backup and restore, reusable consultant baselines, and the unusual development story behind more than 30,000 lines of PowerShell. Andres explains why detailed, published specifications produced better AI-generated code than incremental prompting—and why the intent and edge cases in an open-source contribution matter more than who typed the implementation.
Subscribe with your favorite podcast player or watch on YouTube.
About Andres Canello
Andres Canello is a Principal Product Manager at Microsoft, where he works at the intersection of modern identity and Secure Service Edge. Over his 15 years at Microsoft, he was a founding member of the Entra Global Secure Access team, helping shape the product before it launched, and has since guided some of the largest identity and secure-access deployments in the industry, from banks and miners to national governments. He’s the creator of Migrate2GSA, an open-source migration toolkit used by organizations around the world, which he built end-to-end using AI-assisted, spec-driven development.
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Related Links
* Plan and troubleshoot UserPrincipalName changes in Microsoft Entra ID (mentioned at 04:07)
* Azure AD Mailbag: Conditional Access Q&A by Andres Canello (mentioned at 06:43)
* Migrate2GSA documentation (mentioned at 45:37)
* Migrate2GSA source repository (mentioned at 45:37)
Related Entra.Chat Episodes
* How to Migrate from Legacy VPNs to Entra Private Access (Real Strategies from a Veteran)
* Global Secure Access Explained: Real-World Rollouts, Mistakes, and Best Practices
* Identity-Centric Network Security: Entra Global Secure Access Architecture & Benefits
Chapters
00:00 Intro
01:05 Andres Canello's 15 Years in Microsoft Identity
06:43 A Conditional Access Mistake Admins Still Make
11:29 From Early Customer Pilots to Entra GSA
13:21 Why SSE Migrations Should Not Start From Scratch
18:31 Beyond Migration: Backup Restore and Greenfield
23:27 Export Convert Review and Provision
27:02 How Specifications Made AI-Generated PowerShell Work
35:22 Conflict Detection and the Human Review Gate
39:14 Microsoft Graph Provisioning with Safety Built In
43:35 Automating the Repetitive 80 Percent
46:15 Contributing to Migrate2GSA
Podcast Apps
* YouTube
* Spotify
* Overcast
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* YouTube
* LinkedIn
* Twitter
* TikTok
* Bluesky
* Mastodon
* Threads
* GitHub
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeWhy Entra Admins Need Microsoft Purview Now
Conditional Access no longer begins and ends with identity signals.Microsoft Purview can now influence the controls Entra administrators are asked to implement. From insider-risk conditions in Conditional …
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Conditional Access no longer begins and ends with identity signals.
Microsoft Purview can now influence the controls Entra administrators are asked to implement. From insider-risk conditions in Conditional Access to inline protection for sensitive data moving toward unsanctioned AI apps. That means Entra teams need enough Purview knowledge to understand what triggers a policy, how users experience it, and who should respond when an alert fires.
In this episode of Entra.Chat, Merill speaks with Ray Reyes, Principal Security Consultant at Engage Squared and author of Mastering Microsoft Purview Deployment in the Era of AI. Ray explains Data Loss Prevention and Insider Risk Management in plain language, then follows their integrations into Microsoft Entra ID, Microsoft Defender XDR, and Global Secure Access.
The conversation moves beyond product configuration. A policy can be technically simple and still require identity, network, data-security, HR, management, and data-owner teams to agree on scope, ownership, education, escalation, and remediation. Ray’s practical advice is to understand the neighbouring Microsoft security products at a high level and deploy Purview gradually: start in audit mode or with a limited group, learn from the impact, and expand with the business.
Ray also shares the story of the charity he and his wife started in Nepal, how it grew from supporting roughly 30 street children to reaching thousands, and how that chapter changed his perspective on work and stress. He and Merill close with an honest discussion about burnout, layoffs, gratitude, personal branding, and building a career safety net outside any one employer.
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Subscribe with your favorite podcast player or watch on YouTube.
About Ray Reyes
Ray Reyes is a Principal Security Consultant at Engage Squared and the author of Mastering Microsoft Purview Deployment in the Era of AI. He previously worked at Microsoft, where he led data-security subject-matter expertise across Asia Pacific and Japan and helped customers deploy Microsoft Purview and Microsoft Defender XDR. His work now spans identity, data security, and the wider Microsoft security stack.
* LinkedIn → linkedin.com/in/ray-reyes-598062125
Related Links
* Mastering Microsoft Purview Deployment in the Era of AI by Ray Reyes (mentioned at 00:00 and 02:25)
* Microsoft Purview overview (discussed from 03:29)
* Adaptive Protection in Microsoft Purview (discussed at 22:09)
* Learn about Data Loss Prevention for Network Data Security (discussed at 33:31)
* Configure Microsoft Entra Internet Access content filtering (discussed at 34:18)
* The Resilience Project: Finding Happiness through Gratitude, Empathy and Mindfulness by Hugh van Cuylenburg (mentioned at 47:25)
Related Entra.Chat Episodes
* How Microsoft Is Securing AI Agents in Entra — Conditional Access, Zero Trust & the “Block” Debate
* How to Migrate from Legacy VPNs to Entra Private Access
* What’s New in Microsoft Entra — May 2026: Passkeys, Agents & Cloud Sync
Chapters
00:00 Intro
03:29 Why Purview Matters to Entra Admins
05:39 How Microsoft Purview Evolved
09:46 Data Loss Prevention Explained
16:04 Insider Risk and Employee Departures
22:09 Adaptive Protection Meets Conditional Access
25:00 Education and Alert Ownership
28:51 Breaking Down the Security Silos
33:31 Network Data Security and Unsanctioned AI
38:29 How to Roll Out Purview Safely
41:20 Ray’s Charity Work in Nepal
47:10 Resilience Burnout and a Career Safety Net
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeHow Xbox Secures 70+ Entra Tenants Every Night with Maester
Xbox Security runs a gaming-specific Microsoft Entra baseline across more than 70 tenants every night.The scale is striking: about 50 controls, dozens of independently operated game-studio tenants, and one …
Shownotes
Xbox Security runs a gaming-specific Microsoft Entra baseline across more than 70 tenants every night.
The scale is striking: about 50 controls, dozens of independently operated game-studio tenants, and one parallel pipeline that checks whether each environment still matches Xbox’s security intent. When a Conditional Access policy moves to report-only or a required service principal loses a permission, the next run finds it.
In this episode of Entra.Chat, Merill speaks with Audrey Long, Principal Cloud Security Architect in Xbox Security at Microsoft, and Sam Erde, SecureShield Architect at Patriot Consulting and a Maester maintainer. Audrey explains how Xbox Security extended Maester with custom PowerShell, GitHub Actions, a multi-tenant service principal, federated identity credentials, dashboards, ticketing, and time-bound exceptions.
The result is more than a posture report. Findings flow into an operational lifecycle with owners and deadlines. Studios get readable reports, deep links to the affected object, and remediation guidance. Security teams can answer audit questions without interrupting all the tenant admins, while the Maester pipeline keeps read-only observability separate from remediation authority.
The conversation also covers why a Microsoft-wide baseline needs adapting for gaming acquisitions, how custom tests encode an organization’s intent, why security configuration deserves regression tests, the Investigate status Audrey’s team helped introduce, and how administrators can use AI as a first-draft assistant for PowerShell and CI/CD without outsourcing validation.
Subscribe with your favorite podcast player or watch on YouTube
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* Keep 5+ years of tenant history in your chosen Azure region
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Maester Cloud is in active development. Join the waitlist for hosted, self-hosted, or enterprise onboarding updates.
About Audrey Long
Audrey Long is a Principal Cloud Security Architect in Xbox Security at Microsoft. She focuses on Microsoft Entra and identity security, as well as securing Azure, AWS, and Google Cloud environments across Xbox and its game studios. In this episode, she shares how her team built a gaming-specific Entra baseline and operationalized it across more than 70 tenants.
* LinkedIn - https://www.linkedin.com/in/aulong/
About Sam Erde
Sam Erde is part of the Maester core maintainer team, a Microsoft MVP, and a SecureShield Architect at Patriot Consulting. He focuses on Active Directory, Microsoft Entra ID, Microsoft 365 security, and practical PowerShell tooling for defenders.
LinkedIn - https://www.linkedin.com/in/samerde/
Related Links
* Maester, installation guide, and source code (mentioned at 02:19) - Maester · installation guide · GitHub source
* Continuous monitoring with Maester and GitHub Actions (mentioned at 14:38) - https://maester.dev/docs/monitoring/github/
* Writing custom Maester tests (mentioned at 22:39) - https://maester.dev/docs/writing-tests/
* Connect-Maester permissions and read-only access (mentioned at 24:38) - https://maester.dev/docs/connect-maester/
* Zero Trust Assessment: Secure your tenant (mentioned at 25:46) - https://entra.news/p/find-your-tenants-hidden-flaws-in
* Maester’s Investigate test-result status (mentioned at 34:02) - https://maester.dev/docs/writing-tests/formatting-test-results/
* Making Security Invisible for Game Developers (mentioned at 45:52) - https://opsmatters.com/videos/making-security-invisible-game-developers
Related Entra.Chat Episodes
* How to Secure Copilot Agents, Azure DevOps & Defender (+ more) with Maester 2.1 (Full Breakdown)
* Zero Trust Assessment: Secure your tenant
* How to Design Bullet-Proof Conditional Access Policies in Microsoft Entra ID
Chapters
00:00 Intro00:42 Meet Audrey Long02:19 From 50 Controls to 70+ Tenants05:11 Making an Entra Baseline Gaming-Specific08:32 Why Custom Maester Tests Matter11:07 Governance and Nightly Automation15:27 From Findings to Remediation18:07 Reports Studios Can Actually Use22:39 Building Custom Multi-Tenant Tests28:07 Security Intent as Regression Tests30:48 Catching Drift and Producing Audit Evidence41:39 CI/CD and AI for Security Admins
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeOne Compromised Agent ID Blueprint Can Cross Tenant Boundaries
Microsoft Entra Agent ID uses familiar application and service-principal objects under the hood, but its one-to-many hierarchy creates a different security boundary. A blueprint can be associated with many …
Shownotes
Microsoft Entra Agent ID uses familiar application and service-principal objects under the hood, but its one-to-many hierarchy creates a different security boundary. A blueprint can be associated with many agent identities. When that blueprint belongs to a third-party provider and is trusted across customer tenants, the provider’s credential security becomes part of every customer’s risk model.
In this episode of Entra.Chat, Merill speaks with Katie Knowles, Senior Security Researcher at Datadog, about her three-part security analysis of Microsoft Entra Agent ID. Katie explains the blueprint, blueprint principal, agent identity, and agent-user relationships before walking through a cross-tenant compromise demonstration: compromised blueprint credentials, enumeration of associated agents, token requests in trusting tenants, permission inspection, and selection of a useful target identity.
That path does not automatically grant Global Administrator access. Its impact depends on what the target agent identity has been permitted to do. The important lesson is the control point: one blueprint can sit upstream of many identities, tenants, and permission sets.
Katie and Merill also discuss tenant-owned versus vendor-owned blueprints, the Agent ID Administrator role, first-party agent creation through Microsoft platforms, why production client secrets compound the blast radius, workload identity federation, separating blueprints by risk, reusing app-registration detections, and Microsoft Entra ID Protection for agents.
REGISTER: Hidden Risk of App Permissions in Entra ID
Many Microsoft Entra ID environments contain third-party and custom applications with permissions that are broader than necessary, and most organizations lack visibility into how those permissions are being used. Excessive Microsoft Graph permissions and unused access increase the risk of OAuth abuse and privilege escalation.
Join our live session on July 22 to learn how to:
* Evaluate delegated versus application permissions
* Build an effective app governance strategy
* Reduce unnecessary access without disrupting users
You’ll also see how a free AppGov Score assessment can help identify governance gaps and where unused permissions reporting fit into a least-privilege approach.
Subscribe with your favorite podcast player or watch on YouTube
About Katie Knowles
Katie Knowles is a Senior Security Researcher at Datadog focused on Azure security research, cloud identity, and securing emerging technologies.
* LinkedIn - https://linkedin.com/in/kaknowles
* X/Twitter - https://twitter.com/_sigil
* GitHub - https://github.com/siigil
* Website - https://kknowl.es/
* Microsoft MVP profile - https://mvp.microsoft.com/en-US/MVP/profile/a3547b6a-6a4d-4aa0-840f-23b858c43c8b
Related Links
* Entra Agent ID: The blueprint blast radius (mentioned at 51:39) - https://securitylabs.datadoghq.com/articles/agent-id-blueprint-blast-radius/
* Entra Agent ID: Inside a cross-tenant agent compromise (mentioned at 51:39) - https://securitylabs.datadoghq.com/articles/agent-id-inside-agent-compromise/
* Entra Agent ID: Protect, detect, respond (mentioned at 51:39) - https://securitylabs.datadoghq.com/articles/agent-id-protect-detect-respond/
* Disable agent identities in your tenant (mentioned at 04:00 and 49:33) - https://learn.microsoft.com/entra/agent-id/disable-agent-identities
* Investigating suspicious AI workflows in Microsoft Entra Agent ID: Agent’s user account (mentioned at 05:14) - https://redcanary.com/blog/threat-detection/entra-id-ai-workflows-teams/
* Entra Agent ID from a Security Perspective (mentioned at 20:38) - https://blog.compass-security.com/2026/06/entra-agent-id-from-a-security-perspective/
* Spying On Your ISVs Credential Choices (mentioned at 38:11) - https://ericonidentity.com/2025/01/13/spying-on-your-isvs-credential-choices/
* Who Are the Robots? Uncovering AI Agents Identities (mentioned at 51:39) - https://www.youtube.com/watch?v=mMxACHKIAwY
* AzTier (mentioned at 51:39) - https://aztier.com/
* Microsoft Entra Agent ID key concepts - https://learn.microsoft.com/entra/agent-id/key-concepts
* Workload identity federation - https://learn.microsoft.com/entra/workload-id/workload-identity-federation
* ID Protection for agents - https://learn.microsoft.com/entra/id-protection/concept-risky-agents
Related Entra.Chat Episodes
* If You Manage Entra Permissions, Watch This Before Deploying Agents - https://entra.news/p/if-you-manage-entra-permissions-watch
* From Windows Core to Leading Agent ID: Vince Smith’s Microsoft Story - https://entra.news/p/from-windows-core-to-leading-agent
* Attackers Are Targeting the AI Ecosystem You Cannot See - https://entra.news/p/attackers-are-targeting-the-ai-ecosystem
Chapters
00:00 Intro
01:12 Katie’s Three-Part Agent ID Research
05:40 Agent ID Objects Under the Hood
06:24 One Blueprint, Many Agent Identities
08:43 The Multitenant Trust Boundary
17:33 Cross-Tenant Compromise Walkthrough
28:29 First-Party and Third-Party Blueprints
36:56 Stop Using Client Secrets
38:40 Workload Identity Federation
46:24 Permissions and Privilege Boundaries
49:33 Detecting and Responding to Agent Abuse 51:29 What Comes Next for Agent ID
Podcast Apps
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeAttackers Are Targeting The AI Ecosystem You Cannot See
AI agent security is not just about attackers using AI.It is also about attackers targeting the agent ecosystem most organizations cannot see clearly yet: MCP servers, agent skills, packages, API keys, prompts …
Shownotes
AI agent security is not just about attackers using AI.
It is also about attackers targeting the agent ecosystem most organizations cannot see clearly yet: MCP servers, agent skills, packages, API keys, prompts, tools, and the identity layer underneath all of it.
In this episode, I sit down with Thomas Roccia, founder of Security Break and a former Microsoft threat researcher, to look at AI agents from the threat-intelligence side. Thomas explains why the easiest path for attackers may not be futuristic autonomous hacking. It may be the boring weak spots that already exist: malicious packages, untrusted MCP servers, hostile agent skills, leaked API keys, and AI-generated code that chooses the fastest path instead of the safest one.
For Entra admins and security teams, this is where Agent ID, non-human identity, workload identity, logging, sponsorship, and governance start to matter. Entra Agent ID gives teams a way to identify and govern agents, but identity is only one part of the picture. You still need to understand what agents can discover, what tools they can call, what context they consume, and whether you can replay what they actually did.
Thomas also breaks down his practical AI threat-intelligence work, including how teams can use agents for CTI, how adversarial prompts and context flooding change the risk model, and why defenders need to understand the attacker side of agent security before these systems become invisible production infrastructure.
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About Thomas Roccia
Thomas Roccia is a threat researcher and founder of SecurityBreak, focused on AI threat intelligence, malware analysis, and AI agent security. He previously worked in incident response, malware analysis, threat intelligence, Microsoft Defender, and AI threat research. He is also the author of Visual Threat Intelligence and teaches practical AI for threat intelligence and agentic workflows.
LinkedIn - https://au.linkedin.com/in/thomas-roccia
Subscribe with your favorite podcast player or watch on YouTube 👇
Related Links
* Thomas Roccia on LinkedIn - https://au.linkedin.com/in/thomas-roccia
* SecurityBreak - https://securitybreak.io/
* Practical AI for Threat Intelligence training - https://securitybreak.io/training-genai
* SHIELD.md: A Security Standard for OpenClaw and AI Agents - https://blog.securitybreak.io/shield-md-a-security-standard-for-openclaw-and-ai-agents-b38637031460
* Microsoft Entra Agent ID - https://learn.microsoft.com/en-us/entra/agent-id/what-is-microsoft-entra-agent-id
* Microsoft Entra Agent ID key concepts - https://learn.microsoft.com/en-us/entra/agent-id/key-concepts
* Agentic Resource Discovery specification - https://agenticresourcediscovery.org/
* GitHub Agent Finder - https://github.blog/changelog/2026-06-17-agent-finder-for-github-copilot-now-available/
Chapters
00:00 Intro
00:33 Meet Thomas Roccia
01:48 From Malware Analysis to AI Threat Intel
03:30 Why AI Security Is Moving So Fast
05:49 Agentic Resource Discovery and New Standards
09:25 Attackers Are Already Using AI Agents
11:47 The AI Ecosystem Is The Target
15:26 Prompt Injection, MCP, Skills, and API Keys
20:28 Vibe Coding vs Production Security
23:47 Agent ID and Identity for AI Agents
32:30 Practical AI for Threat Intelligence
39:13 Monitoring Agents Like Threat Actors Do
42:28 Context Flooding and What’s Next
Podcast Apps
Apple Podcast - https://entra.chat/apple
YouTube - https://entra.chat/youtube
Spotify - https://entra.chat/spotify
Overcast - https://entra.chat/overcast
Pocketcast - https://entra.chat/pocketcast
Others - https://entra.chat/rss
Merill’s socials
YouTube - youtube.com/@merillx
LinkedIn - linkedin.com/in/merill
Twitter - twitter.com/merill
TikTok - tiktok.com/@merillf
Bluesky - bsky.app/profile/merill.net
Mastodon - infosec.exchange/@merill
Threads - threads.net/@merillf
GitHub - github.com/merill
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeFrom Windows Core to Leading Agent ID: Vince Smith’s Microsoft Story
Folks, every big thing in identity started as somebody’s late-night side quest and Vince Smith has been in the room for a lot of them. In this episode of Entra Chat, Vince (the PM lead driving Microsoft Entra …
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Folks, every big thing in identity started as somebody’s late-night side quest and Vince Smith has been in the room for a lot of them.
In this episode of Entra Chat, Vince (the PM lead driving Microsoft Entra Agent ID) walks us back through a 25-year run at Microsoft: shipping beta products off a machine wired straight to the internet under a neighbor’s desk, owning the early RBAC and custom roles work that shaped Entra, surviving a couple of security incidents he mostly can’t talk about, and finally landing on the team building identity for AI agents.
Along the way he owns up to the one feature name he’d take back if he could, and shares the dead-simple trick he used as a junior dev to get senior engineers to answer his questions every single time.
But this isn’t just a war-stories episode. Vince breaks down why agents needed a brand-new kind of identity in the first place. An agent is a strange beast ‘as clumsy and unpredictable as a human, and as fast as a machine’ which means traditional anomaly detection looks at one and basically can’t tell if it’s a user or a workload gone rogue. His answer is the blueprint-and-instance model: one blueprint (think app registration) spinning up many scoped, least-privilege instances, instead of a bazillion app registrations or one over-permissioned service principal that can read everyone’s mailbox. And if you’re wondering why this matters now, Vince makes the case that as users move to passkeys, attackers just slide to the other end of the balloon: non-human identities and workloads. That’s the new frontier.
So what should you actually do Monday morning? His advice is refreshingly un-precious: don’t wait for the perfect plan. Start green, set a standard for every new agent so you stop the bleeding from shadow AI, then stay green and slowly get green by cleaning up the mess behind you. Even just stamping a unique identifier on your agents today buys you the observability you’ll desperately want later.
Be the river that flows around the rocks.
There’s a lot more in the full conversation including how Agent ID and Agent 365 actually fit together, and how Vince came up to speed on a space that’s moving too fast to write a book about. Give it a watch.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Vince Smith
Vince Smith is the PM Lead for Agent ID at Microsoft. A self-described computer nerd and Gen Xer, Vince has been with Microsoft since late 1999, working on everything from Windows Core and GDPR to multi-tenant collaboration and identity protection.
LinkedIn - https://www.linkedin.com/in/vincecsmith/
🔗 Related Links
* Entra Agent ID - https://learn.microsoft.com/en-us/entra/agent-id/what-is-microsoft-entra-agent-id
* Agent 365 - https://www.microsoft.com/en-us/microsoft-agent-365
📗 Chapters
06:23 Provisioning vs. Federation
10:25 The Need for Agent ID
17:28 Blueprints and Multi-Instancing
23:55 Demystifying Agent 365
26:56 The Threat of Non-Human Identities (NHI)
33:08 Planning Your Enterprise AI Strategy
36:14 Defining a “Start Green” AI Plan
40:45 The Best Way to Learn Complex Tech
45:13 The Wild World of CIAM
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
📺 YouTube → https://entra.chat/youtube
📺 Spotify → https://entra.chat/spotify
🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeShadow Admins: The Non-Human Identities Hiding in Your Entra Tenant
Not every admin in your tenant is a person. Service principals, app registrations, and the new wave of agent identities can quietly hold permissions powerful enough to own your entire environment and most orgs …
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Not every admin in your tenant is a person. Service principals, app registrations, and the new wave of agent identities can quietly hold permissions powerful enough to own your entire environment and most orgs can’t even see them. In this episode of Entra Chat, we sits down again with Erika Zellig to expose the “shadow admins” hiding in your Entra tenant, and what to do about them.
What we get into:
* Application vs. delegated API permissions and why both can be shadow admins
* The most dangerous permissions to hunt for: Files.ReadWrite.All, Sites.FullControl.All and more.
* How Midnight Blizzard turned secrets buried in email into full tenant compromise
* Credential and secret sprawl why you should vault everything and move to managed identities
* Agent identities explained, and why a “sponsor” is safer than an “owner”
* App ownership as an attack path: lateral movement and privilege escalation
* Locking down workload identities with conditional access
* Deadlines that bite: EWS retirement and the ID CRL protocol retirement
* Managed devices, and going from Zero Trust to “hero trust” without burying your help desk
Subscribe with your favorite podcast player or watch on YouTube 👇
Sponsored by:
Avoiding Entra Credential Outages & Security Risks June 24 | Live Webinar | Register
An expired client secret or certificate can break SSO, automation, integrations, and business-critical applications without warning.
Do you know:
✔️ Which credentials have already expired?
✔️ Which applications depend on them?✔️Which credentials will expire next? ✔️Who owns those applications, and are they still used?
Which applications should use Managed Identities instead of secrets?
As organizations deploy more apps, automations, and AI-powered services, credential sprawl continues to grow across Entra. Join MVPs Alistair Pugin and Nicolas Blank as they walk through real-world credential failures, hidden risks, and practical strategies for identifying and remediating Entra credential issues before they lead to outages, security exposures, or audit findings.
About Erika Zelic
Erika Zelic is a well-known voice in the Microsoft security and identity community, bringing years of offensive security experience to help admins secure their cloud infrastructure.
With roots in offensive security and consulting, she now works on remediating configuration-based vulnerabilities and is known for sharing practical, no-nonsense security insights with the Entra community.
LinkedIn - https://www.linkedin.com/in/erica-z-b4169598/
🔗 Related Links
• MS Identity Tools - https://aka.ms/msid
📗 Chapters
* 02:05 The High Cost of DIY AI & Small Language Models
* 06:17 Why AI is Forcing Everyone to Harden Their Infrastructure
* 14:12 The Hidden Dangers of API Permissions
* 20:59 How Midnight Blizzard Exploited App Secrets
* 27:21 The Magic of Managed Identities & Azure Arc
* 33:38 The Nightmare of Multiple App Owners
* 43:32 Sneaky API Permissions You Need to Monitor
* 51:48 Crucial Protocol Retirements: EWS & ID CRL
* 55:24 Zero Trust: Why You MUST Enforce Managed Devices
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
📺 YouTube → https://entra.chat/youtube
📺 Spotify → https://entra.chat/spotify
🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeHow Microsoft Is Securing AI Agents in Entra - Conditional Access, Zero Trust & the "Block" Debate
AI agents can make decisions and act faster than any human — which means your old identity security playbook no longer holds. In this episode of Entra Chat, [host name] sits down with Nikhil, a 10+ year …
Shownotes
AI agents can make decisions and act faster than any human — which means your old identity security playbook no longer holds. In this episode of Entra Chat, [host name] sits down with Nikhil, a 10+ year Microsoft identity veteran from the Authentication Stack and Identity Protection team, to break down how Microsoft Entra, Conditional Access, Defender, and Purview are evolving to secure agentic AI.
We get into why “security = MFA” is dead, why the only recommended Conditional Access control for agents today is block (and why that’s actually good for your users), the missing “challenge” state in agent access, indirect prompt injection, and the unified risk model spanning identity, endpoint, and data layers. If you manage Microsoft Entra ID, run Zero Trust, or are figuring out how to govern AI agents in your tenant, this one’s for you.
🔎 What you’ll learn:
* Why agents are the new insider threat and why latency no longer protects you
* How Conditional Access now targets agentic users and agents
* Why “block” is the default control for agents (allow / block / challenge explained)
* How unified risk works across Entra, Microsoft Defender & Microsoft Purview
* Continuous Access Evaluation interrupting in-motion agent sessions
* Why LLMs recommend insecure defaults (the device code flow problem)
* The Conditional Access optimization agent, report-only mode & phased rollout
* The #1 thing Entra admins and CISOs should do in the next 3–6 months
Subscribe with your favorite podcast player or watch on YouTube 👇
About Nikhil
Nikhil Boreddy has spent over a decade at Microsoft, from the early Authentication Stack and Identity Protection team to the birth of Conditional Access. Today he works across Entra and Microsoft Security on one of the toughest challenges in the field: securing AI agents in the enterprise.
LinkedIn - https://www.linkedin.com/in/nikhilboreddy/
🔗 Related Links
* Microsoft Entra - https://learn.microsoft.com/en-us/entra/id-protection/concept-risky-agents
* Microsoft Zero Trust - https://aka.ms/ztworkshop
📗 Chapters
00:01:49 The Shift from MFA to Zero Trust
00:02:43 The Rise of AI Agents in Enterprise Security
00:04:40 Vulnerabilities in AI Workflows
00:08:09 Microsoft Security and Agent ID
00:10:41 Using the Conditional Access Optimization Agent
00:11:44 Breaking Silos: Entra, Purview, and Defender
00:20:01 Expanding Conditional Access for Agentic Users
00:26:36 Why Block is the Recommended Control for Agents
00:33:38 The Power of the Microsoft Security Stack
00:38:31 Advice for CISOs: Embracing AI in Security
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
📺 YouTube → https://entra.chat/youtube
📺 Spotify → https://entra.chat/spotify
🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeThe Learn-It-All Career Playbook for Identity and Security Pros
In this episode of Entra Chat, we sit down with Christina Morillo, the Senior Director of Information Security for the New York Football Giants, to explore her inspiring transition from an identity specialist …
Shownotes
In this episode of Entra Chat, we sit down with Christina Morillo, the Senior Director of Information Security for the New York Football Giants, to explore her inspiring transition from an identity specialist to a top-tier security leader. Christina shares her “ground floor” start at a technical help desk and her progression through network administration and specialized identity roles at Microsoft. Her story is a powerful testament to the “learn-it-all” mindset, illustrating how a deep baseline in Active Directory and a genuine curiosity about the broader security landscape paved the way for her current leadership role in a high-profile organization.
The conversation dives deep into the essential skills required to grow from a niche technical role into a broader Director or CISO position. Christina emphasizes that while technical proficiency is the foundation, “soft skills” such as storytelling and the ability to pitch security solutions as business value are what truly allow a leader to secure executive buy-in. She encourages professionals not to restrict themselves to one domain but to embrace both breadth and depth, leveraging community engagement to understand the shared struggles across different security verticals.
Subscribe with your favorite podcast player or watch on YouTube 👇
Sponsored by:
Entra ID Credential Gaps That Cause Outages
In Microsoft Entra ID, outages often start small: an expired client secret, or a lapsed certificate quietly breaks an integration. Traditional controls don’t easily track credential expiry, so issues surface only after something fails. Teams are left asking:
* Which app secrets are expiring and when?
* Which certificates are at risk?
* How many integrations are we managing?
Unanswered, these questions lead to avoidable outages, spikes in service desk tickets, and users losing access and bringing projects to a halt. ENow AppGov Credential Monitor continuously tracks expiring secrets and certificates across your Entra ID apps, alerting your team before credentials expire and integrations fail. Get a 7-day free trial to see how it can help you stay ahead.
About Christina Morillo
Christina Morillo is a seasoned cybersecurity and technology executive with over two decades of cross-domain experience leading enterprise security, cloud architecture, and identity programs. As an Information Security Officer and trusted advisor, and in her current role as Senior Director of Information Security at The New York Football Giants, she blends technical depth with strategic leadership to drive resilience, regulatory alignment, and business impact.
Her career spans diverse industries, including financial services, big tech, and professional sports, bringing a unique perspective to every challenge. Christina is also a published O’Reilly author (Zero Trust Networks: Second Edition & 97 Things Every Information Security Professional Should Know) and is passionate about making security and technology accessible, relatable, and actionable for all.
LinkedIn - https://www.linkedin.com/in/christinamorillo/
📗 Chapters
00:00 Intro Chat
00:21 Meet Christina Murillo
01:38 From Helpdesk to Identity
05:40 Discovering the World of Security
07:26 Transitioning to a Broader Security Role
11:47 The Power of Curiosity and Collaboration
19:31 Embracing AI and New Technologies
22:01 Storytelling and Pitching to Executives
28:24 Adapting to Constant Industry Change
32:41 Tailoring Career Advice for Today’s World
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
📺 YouTube → https://entra.chat/youtube
📺 Spotify → https://entra.chat/spotify
🎧 Overcast → https://entra.chat/overcast
🎧 Pocketcast → https://entra.chat/pocketcast
🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
🕺 TikTok → tiktok.com/@merillf
🦋 Bluesky → bsky.app/profile/merill.net
🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribe5 Lessons from Rolling Out Passkeys to Millions of Users
Passkeys are one of those technologies that sound simple on paper.Turn them on.Users register them.Passwords go away.Everyone is more secure.But in the real world, passkey rollouts are not just an …
Shownotes
Passkeys are one of those technologies that sound simple on paper.
Turn them on.Users register them.Passwords go away.Everyone is more secure.
But in the real world, passkey rollouts are not just an authentication setting. They are a product rollout, a user experience change, a support change, and an operational change all at once.
In this episode, I spoke with Vincent Delitz from Corbado, who has worked on large-scale passkey deployments in customer identity scenarios, including public-sector and consumer environments with millions of users. While the examples come from the CIAM world, many of the lessons apply directly to workforce identity and Microsoft Entra deployments as well.
Sponsored by:
Cloud RADIUS built for Entra + Intune environments
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* Deploy in minutes: no on-prem servers, no Windows updates
* Certificate-based auth: EAP-TLS support for Microsoft Cloud PKI or any CA
* Intune compliance checks for zero-trust Wi-Fi and VPN access
* Built for teams of 10 to 10,000: no minimums, no enterprise gatekeeping
* Pay only for users that connect with usage-based pricing
Start your 30-day trial (no credit card required) or book a demo to see how “EZ” it is.
Here are five practical lessons from the conversation.
1. Know why you are rolling out passkeys
Before you start the rollout, be clear on the reason.
Most organisations adopt passkeys for one or more of these reasons:
SecurityPasskeys are phishing-resistant and remove many of the risks that come with passwords, SMS OTP, and other phishable methods.
User experienceSigning in with Face ID, Touch ID, Windows Hello, or a security key can be faster and easier than typing passwords and completing MFA prompts.
Cost reductionIn customer identity scenarios, passkeys can reduce SMS OTP costs. In workforce scenarios, they can reduce password reset and sign-in related help desk calls.
The key lesson is this: your rollout strategy should match your goal.
If your goal is security, you need to think about when and how to retire phishable methods.If your goal is adoption, you need to make passkeys the easiest path.If your goal is cost reduction, you need to measure whether users are actually moving away from the older methods.
Simply enabling passkeys is not the same as achieving the outcome.
2. Use a staged rollout, not a big bang
One of the biggest mistakes is assuming you can turn on passkeys and immediately remove passwords.
That sounds clean from a security perspective, but in reality it can create confusion, support tickets, and failed sign-ins.
A better model is a staged rollout:
Stage 1: Offer passkeys as an option
Start by making passkeys available. Let users register and begin using them without taking away existing methods immediately.
Stage 2: Nudge adoption
Do not leave passkeys buried as “just another sign-in method.” Make them visible. Make them the preferred option where possible. Help users understand why they should use them.
Stage 3: Gradually retire phishable methods
Once you can see that a user or group has been successfully using passkeys for a period of time, then you can start reducing reliance on passwords, SMS, or other weaker methods.
Stage 4: Fix recovery
This is the part many teams forget.
Once passkeys become the primary sign-in method, account recovery becomes the new weak point. If recovery still relies on phishable methods or manual help desk processes, attackers will target that path instead.
A passkey rollout is not complete until recovery is also secure.
3. Passkeys move complexity from the backend to the user’s device
With passwords, SMS OTP, or push notifications, a lot of the complexity sits in the backend.
With passkeys, much more happens on the client side.
That means success depends on things like:
The user’s device.The browser version.The operating system.The credential manager.Whether Bluetooth is enabled.Whether the passkey is synced.Whether the user is on a managed device or BYOD.Whether a password manager has changed the sign-in experience.
This is a big mindset shift.
For example, cross-device passkey sign-in often relies on Bluetooth proximity checks. That is great when it works. But what happens if Bluetooth is disabled on a kiosk, blocked by policy, or unavailable on a shared device?
In the episode, we discussed a real-world example where a rollout assumed passkeys would work for retail staff using shared kiosks, only to discover later that Bluetooth was disabled in that environment.
That is the sort of issue you want to find before go-live, not after a three-month project.
The practical takeaway: test the real environments your users will sign in from. Not just your own managed test devices.
4. Your backend logs may not tell the full story
This was one of the most important lessons from the episode.
Passkey success rates can look great in backend logs, but still miss a large part of the user experience.
Why?
Because many failures happen before the backend sees anything useful.
A user may not have the passkey on the current device.The credential manager may not appear.The browser may have a bug.The user may cancel the Face ID or Touch ID prompt.The passkey may have been deleted locally.The device may try to use the wrong credential manager.The user may think registration worked, even though the backend blocked it.
From the backend, you might only see the successful challenges. That can make your success rate look much better than the lived experience.
This is why observability matters.
For customer identity platforms, you may be able to add frontend telemetry and track where users get stuck. In workforce scenarios, you may not be able to instrument the Entra sign-in page directly, but you can still look for signals elsewhere:
Which users are passkey-capable?Which devices and browsers are being used?Which users registered passkeys but are not using them?Which support tickets map to specific OS, browser, or credential manager combinations?Which groups are still falling back to passwords or SMS?
The lesson: do not rely on a single “success rate” number. It may hide the real rollout problems.
5. Support multiple passkeys and explain the mental model
A common mistake is limiting users to one passkey.
That may sound tidy, but it does not match how people actually work.
A user may have a Windows laptop, a Mac, an iPhone, an Android phone, a password manager, and a physical security key. Some passkeys sync. Some do not. Some are device-bound. Some are stored in iCloud Keychain, Google Password Manager, Bitwarden, 1Password, Windows Hello, or on a physical key.
If users can only register one passkey, they may be locked out when they move to another device.
A better approach is to allow multiple passkeys and make it clear what each one is for.
For example:
One passkey in iCloud Keychain.One in Google Password Manager.One in an enterprise password manager.One physical security key.One backup key for critical accounts.
This also means communication matters.
Users do not always understand terms like “FIDO2,” “WebAuthn,” “AAGUID,” “attestation,” or even “passkey.” They understand things like:
Sign in with your face.Sign in with your fingerprint.Use your security key.Use the passkey saved on this device.
The more technical your language, the more likely users are to get confused.
This applies internally as well. Even project teams need a shared vocabulary. Are you talking about synced passkeys? Device-bound passkeys? Security keys? Windows Hello for Business? Platform credentials? Roaming authenticators?
If the project team is confused, the users definitely will be.
Bonus lesson: Attestation matters, but not for every user
We also discussed attestation, which is one of those topics that can get confusing quickly.
In simple terms, attestation lets an authenticator …
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeThe New Control Plane for Microsoft Entra Tenant Governance
Microsoft had 7 million internal tenants and almost lost control of their environment and your org might be facing the same problem at a smaller scale. In this episode, we sit down with Jeff Staiman, PM Area …
Shownotes
Microsoft had 7 million internal tenants and almost lost control of their environment and your org might be facing the same problem at a smaller scale. In this episode, we sit down with Jeff Staiman, PM Area Lead for Tenant Governance at Microsoft, to break down the feature born from the Midnight Blizzard attack. We cover discovery, drift detection, governance relationships, secure tenant creation, licensing, and exactly where admins should start.
What Can Your AI Applications Access?
Organizations are investing heavily in AI-powered applications and agents, but many are discovering they lack the operational visibility and governance discipline needed to scale AI confidently and securely.
With continuous visibility into Entra ID applications, permissions, OAuth access, secrets, certificates, and application ownership, ENow App Governance Accelerator can:
* Reduce uncertainty around what SaaS apps can access
* Accelerate application reviews and approval processes
* Strengthen operational trust across security and leadership teams
* Prevent unmanaged application growth from becoming operational risk
* Enable lean IT teams to support AI expansion at scale
* Demonstrate governance maturity required for enterprise AI adoption
While most admins focus on securing their primary production environment, many organizations are sitting on hundreds of “test” or “shadow” tenants that were created by users with a simple Azure subscription. These unmanaged environments often lack proper security bars and can become entry points for sophisticated attackers.
The Wake-Up Call: Midnight Blizzard
The urgency for these new features was fueled by the 2024 Midnight Blizzard attack. In that instance, attackers compromised a legacy test tenant and used its old access rights to move laterally into Microsoft’s core environment. This highlighted a critical gap: securing one tenant isn’t enough if you don’t even know how many other tenants are connected to your organization.
Three Things You’ll Learn in This Episode:
* Automatic Discovery of the “Unknown”: Jeff explains how the Related Tenants feature uses signals like B2B sign-in logs, multi-tenant app consents, and billing relationships to automatically find every tenant connected to your corporate identity.
* Configuration Drift Monitoring: You can now define a “Golden Configuration” for your tenants. The service monitors over 200 resource types across Entra, Intune, Teams, and Exchange every six hours, alerting you the moment a security setting is weakened.
* The “Three-Step” Handshake: To prevent accidental or malicious takeovers, Microsoft has implemented a rigorous trust process. If two tenants don’t share a billing relationship, the governed tenant must explicitly invite the governing tenant before any control can be established.
A New Approach to Licensing
Something many admins will find surprising is the licensing model. Unlike many Entra features that require a license for every user, Tenant Governance is licensed based on the number of admins interacting with the features. This makes it far more accessible for organizations trying to secure a massive multi-tenant estate without a massive budget.
Why you should listen: Jeff dives deep into how Microsoft managed its own 7 million internal tenants and shares the roadmap for future discovery signals, including using Global Secure Access network telemetry to find tenants being accessed from corporate devices.
Whether you are managing a merger or just trying to clean up years of “test” environments, this episode provides the blueprint for moving from manual, one-tenant-at-a-time management to a deterministic, automated security posture.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Jeff Staiman
Jeff Stammen is the PM Area Lead for Tenant Governance within the Identity and Access Management (IAM) team at Microsoft. A true company veteran of 31 years, Jeff originally joined Microsoft managing engineering compensation and famously architected Microsoft's core engineering leveling framework (Levels 59–61) directly from requirements delivered by Steve Ballmer. Today, he leads engineering and product efforts to secure multi-tenant cloud ecosystems at massive scale.
LinkedIn - https://www.linkedin.com/in/jeffstaiman/
🔗 Related Links
* Microsoft Entra Tenant Governance - https://learn.microsoft.com/en-us/entra/id-governance/tenant-governance/overview
📗 Chapters
00:00 Intro
00:18 Introducing Jeff Stammen
00:41 Jeff’s 31-Year Journey at Microsoft
01:25 The Midnight Blizzard Hack That Started It All
05:07 Tenant Governance: What It Is and Why It Exists
07:12 Where Should Admins Start?
09:57 Configuration Snapshots and Baselines
13:02 The M365 DSC Connection
15:18 What Resources Should You Monitor?
17:07 How Drift Detection Works
19:49 Multi-Tenant Monitoring Strategy
20:02 Related Tenants: Discovering Your Unknown Exposure
20:39 Licensing: Basic vs Premium Explained
22:48 Quotas and Resource Limits
24:27 Governance Relationships and Cross-Tenant Role Assignments
28:26 Two-Step vs Three-Step Governance Flow
31:15 Discovery Signals and Blind Spots
35:17 Tenant Restrictions: A Related Feature Worth Knowing
36:40 Secure Tenant Creation
38:10 Governance Policy Templates
40:01 Licensing Across Multiple Tenants
43:43 Final Recommendations: Where to Start Today
47:54 Wrap Up
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeWhat’s New in Microsoft Entra - May 2026: Passkeys, Agents & Cloud Sync
Fabian and Thomas join the podcast to share their extensive experience and unpack the massive wave of updates coming to Microsoft Entra.We talk about the massive shift toward Passkeys and registration …
Shownotes
Fabian and Thomas join the podcast to share their extensive experience and unpack the massive wave of updates coming to Microsoft Entra.
We talk about the massive shift toward Passkeys and registration campaigns, the impending migration from Entra Connect Sync to Cloud Sync, and the rapidly evolving world of Agent IDs and AI workloads. We also cover how Entra admins can leverage new Defender XDR features and Security Copilot agents to secure their environments.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Fabian and Thomas
Fabian Bader is a Microsoft MVP and Cybersecurity Architect at glueckkanja, based in Hamburg, Germany. He is a well-known researcher in the Microsoft identity space, creator of the Cloud Brothers blog, and creator of the Maester and Token Tactics V2 tools. His work focuses on Microsoft Entra and the Defender suite, helping customers secure their cloud environments.
Thomas Naunheim is a Microsoft MVP and a Cybersecurity Architect at glueckkanja. He specializes in Microsoft Entra, identity and access management, and cloud security posture.
* Thomas LinkedIn - https://www.linkedin.com/in/thomasnaunheim/
* Fabian LinkedIn- https://www.linkedin.com/in/fabianbader/
🔗 Related Links
* What’s New in Microsoft Entra: May 2026 - https://techcommunity.microsoft.com/blog/microsoft-entra-blog/whats-new-in-microsoft-entra-may-2026/4517884
* Claude API Docs - https://platform.claude.com/docs/en/manage-claude/wif-providers/azure
* Microsoft Graph - https://learn.microsoft.com/en-us/graph/api/resources/agentid-platform-overview?view=graph-rest-1.0
📗 Chapters
00:00 Intro
01:18 The Year of Passkeys & Registration Campaigns
08:49 Windows Hello & Passkey Syncing
16:37 Migrating to Entra Cloud Sync
22:27 The Rise of Agent IDs & AI Workloads
28:21 Defender XDR Updates for Entra Admins
38:32 Security Copilot & Conditional Access Agent
45:48 Access Packages & New AI Admin Roles
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeIf You Manage Entra Permissions, Watch This Before Deploying Agents
Microsoft Entra Agent ID Just Went GA Here’s What You Need to Know About Agent PermissionsIf you’ve been waiting for the dust to settle on Microsoft Entra Agent ID before diving in, the wait is over. Agent ID …
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Microsoft Entra Agent ID Just Went GA Here’s What You Need to Know About Agent Permissions
If you’ve been waiting for the dust to settle on Microsoft Entra Agent ID before diving in, the wait is over. Agent ID hit General Availability on May 1st, and in this episode of Entra Chat, Erin Greenlee, a PM in the the Entra AuthN team joins to break down one of the trickiest parts of the new model: how permissions actually work.
The three-tier model you need to understand
The biggest mental shift with Agent ID is moving from the familiar single app registration model to a three-tier hierarchy. Here’s the short version:
* Agent Blueprint → the template for your agent. Think of it as a souped-up app registration that lives in one tenant and defines how the agent behaves. Every agent needs one, even if you’re only ever creating a single instance.
* Blueprint Principle → the identity that represents the blueprint inside each tenant it’s deployed to. This is the middle tier, and it has a superpower: permissions granted here cascade down to all current and future agent identity instances automatically.
* Agent Identity → the actual running instance of the agent. This is what authenticates, what shows up in your tenant logs, and what can hold its own individual permissions on top of whatever it inherits.
Required Resource Access is a hint, not a grant
One thing that trips people up early: adding permissions to the blueprint’s Required Resource Access (RRA) doesn’t actually grant anything. It’s a signal to admins adopting your agent. A polite list of “here’s what this agent will need to function.” The real grant happens later, either upfront during adoption or dynamically as the agent needs it. Expect agents to lean more on dynamic consent than traditional apps have, since agents evolve and request new permissions as tasks change.
Inheritance only works if you set it up
Permissions granted on the Blueprint Principle will only cascade down to agent identities if the resource app (e.g. Microsoft Graph) is explicitly marked as an inheritable resource on the blueprint. It’s an easy thing to miss, and if you skip it, your Blueprint Principle grants won’t flow through to your instances.
A free tool to visualise all of this
Erin built an interactive web app — using GitHub Copilot, no less — that makes all of the above click visually. It has a no-sign-in tutorial that walks you through the object relationships, a permission matrix view, and even generates the PowerShell or Graph API scripts to apply your configuration in real life. No changes are made to your tenant unless you explicitly ask it to. The source code is being open-sourced too, so you can fork and customise it if you want.
Watch the full episode to see Erin walk through the tool live, including how permission inheritance works in practice and a real-world debugging scenario that inspired the whole thing.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Erin Greenlee
Erin is a member of the Entra AuthN team working on AI and Agent ID at Microsoft. She previously joined Entra Chat to discuss app permissions and consent, and she loves building tools that make complex identity concepts easier to understand.
LinkedIn - https://www.linkedin.com/in/eringreenlee/
Sponsored by:
Find App Access Gaps Before They Break Workflows
In Microsoft Entra ID, small visibility gaps lead to outages and delays. Expired secrets break integrations, while unclear ownership and excessive permissions slow access decisions. Teams still struggle to answer:
* Which apps access Microsoft 365 data?
* Is that access still justified?
* Who owns it?
AppGov Score helps you quickly identify these gaps. ENow App Governance Accelerator then exposes app-specific credential risks, permission issues, and ownership gaps before they disrupt operations.
Start with your AppGov Score, then upgrade to a 7-day free trial to take action.
🔗 Related Links
* https://aka.ms/erins-agent-helper
📗 Chapters
01:11 Agent ID General Availability
04:14 The Agent ID Visualizer Tool
05:35 Defining the Agent Blueprint
08:06 Understanding the Blueprint Principle
10:57 Agent Identity Instances Explained
13:37 Required Resource Access (RRA)
24:07 Inheritable Permissions and Cascading
30:18 Applying Changes with Scripts
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeHow to Secure Copilot Agents, Azure DevOps & Defender (+ more) with Maester 2.1 (Full Breakdown)
Maester is back with one of its biggest release since launch. In this episode, we are joined by Sam Erde, Architect at Patriot Consulting and one of Maester’s core maintainers, to walk through everything that’s …
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Maester is back with one of its biggest release since launch. In this episode, we are joined by Sam Erde, Architect at Patriot Consulting and one of Maester’s core maintainers, to walk through everything that’s landed in Maester 2.1.
Since the December release, the community has shipped 540 new commits, grown the test suite from 128 to 168 tests, and added coverage across entirely new product areas.
Here’s a taste of what’s covered:
🤖 Securing Your AI Agents (Copilot Studio) With Microsoft’s Agent 365 going GA and organisations rapidly deploying Copilot Studio agents, Maester now includes tests based directly on Microsoft’s own recommendations for securing agents. Think orphaned agents with no owner, missing authentication on MCP connections, dormant agents, risky HTTP configurations, and agents shared too broadly. If you’re deploying agents in your tenant, these tests should be running.
🔧 AI That Writes Its Own Security Tests One of the most exciting developments in this release isn’t a test, it’s a custom AI skill that writes Maester tests for you. Sam built a GitHub Copilot agent skill that understands Maester’s structure, coding conventions, and contributor guide. You describe a security check in plain English, and within minutes you get a properly structured test, helpers, and documentation. No VS Code required! You can do it straight from GitHub’s Agents tab or even the mobile app. The barrier to contributing to Maester just got a lot lower.
🛡️ Defender for Endpoint Coverage Maester now includes 24 community-contributed MDE tests covering antivirus configuration, endpoint policy posture, cloud protection, behaviour monitoring, and PUA protection. Getting these tests into shape required the new AI skill to refactor months of pending work and it delivered.
🔑 Azure DevOps Security (37+ New Tests) With AI-generated code accelerating supply chain risks, securing your DevOps pipeline has never been more critical. Maester 2.1 ships with 37+ new Azure DevOps tests, checking OAuth config, PAT token policies, external guest access, collection admin hygiene, and more.
🔗 Linked Identity Checks for Privileged Accounts A new test surfaces a common blind spot: privileged admin accounts that remain active after their linked standard user account is disabled. If someone leaves your organisation and their cloud admin account stays enabled, Maester will now catch it.
📋 CIS Benchmark Refresh & Conditional Access Improvements Community contributor Morten has refreshed the CIS benchmark tests to reflect the latest changes, plus improved the logic behind several conditional access policy checks — including automated tracking of Entra ID roles used in XSPM and commercial access quality checks.
There’s a lot more covered in the full episode, including multi-tenant reporting updates, the new dev container for contributors, a surprisingly entertaining story about two AI models dissing each other’s code reviews, and a teaser for what’s coming in the next release.
👉 Listen to the full episode for the deep dives, the war stories behind getting community PRs across the line, and Merill and Sam’s take on where AI fits into the future of security testing.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Sam Erde
Sam is an Architect at Patriot Consulting who focuses on performing security assessments, securing and deploying Microsoft 365, and writing PowerShell. He has been a critical pillar for the Maester community over the last year, helping heavily refactor the codebase and streamlining community contributions.
LinkedIn - https://www.linkedin.com/in/samerde/
Sponsored by:
Would you bet your reputation on your current Microsoft 365 security posture?
Sure, you’ve checked Purview. Maybe tightened Conditional Access. We all do that.
But it’s usually the quiet stuff that bites... permissions that expanded, policies that drifted, exceptions nobody revisited.
You could assume it’s fine.
Or you could run the Microsoft 365 Security Posture Check.
It’s free.
It runs locally.
And no, it doesn’t send your tenant data back to us.
We’ll even help you set it up.
🔗 Related Links
* What’s new in Maester 2.1.0 - https://maester.dev/blog/whats-new-since-maester-2-0
📗 Chapters
00:00 Intro
05:49 Securing Copilot Studio & AI Agents
08:53 The Challenge with Defender for Endpoint Tests
013:39 Using AI to Automate Writing Security Tests
22:30 Dev Containers for Easy Contributions
24:58 New Azure DevOps Security Checks
31:02 Multi-Tenant Reporting & Xbox’s Secret
37:00 Active Directory Tests & The Future of Hybrid
43:00 The Long-Term Vision for Maester
54:48 CIS Benchmarks & Linked Identity Tests
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeWhat an ID Governance Consultant Wishes You Knew About Entra
Identity Governance is often treated as a “nice-to-have” compliance checkbox, but as ID Governance expert Sandra Saluti reveals, it is actually the foundation of a secure, scalable environment. In this …
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Identity Governance is often treated as a “nice-to-have” compliance checkbox, but as ID Governance expert Sandra Saluti reveals, it is actually the foundation of a secure, scalable environment. In this technical deep dive, we move past the marketing slides to discuss some of the common real-world “gotchas” that break Entra ID deployments.
In this episode, you will learn:
* The Golden Rule of Automation: Why you must stop using “presentation data” (like UPNs or Email addresses) as your anchor. We explain why the Object ID is the only immutable truth for your automation.
* The “Marriage Bug”: A cautionary tale of how a simple name change can break hybrid joins and lead to accidental laptop wipes and how to prevent it.
* The “Unsexy” Side of Governance: Why the most important part of your job isn’t writing PowerShell, but interviewing HR and stakeholders to map out process flow diagrams before you ever touch the portal.
* Closing the “Rehire Gap”: How to solve the common crisis where contractors lose access for 48 hours during a renewal because of lifecycle synchronization delays.
* Directory Extensions vs. Exchange Attributes: Technical advice on where to store your identity metadata for the most reliable governance.
Sponsored by:
Entra ID Gaps That Cause Outages
In Microsoft Entra ID, outages often start small: an expired client secret, a lapsed certificate, or a suddenly failing integration. Traditional controls don’t track credential expiry or enforce application ownership, so issues appear only after something breaks.
Teams are left asking:
* Which applications can access Microsoft 365 data?
* Is that access still appropriate?
* Who owns the app?
Unclear answers stall reviews, weaken accountability, and slow delivery.
ENow App Governance Accelerator closes these gaps by highlighting expiring credentials, surfacing permission risks, and identifying ownership gaps before they disrupt operations. New Standard Tier pricing makes it accessible for organizations under 10,000 users, typically $3,500–$9,500 annually.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Sandra Saluti
Sandra Saluti is a consultant at Epical working with Microsoft Entra ID and identity governance. She helps organisations design secure and practical identity solutions with a focus on governance, access management, and Zero Trust.
LinkedIn - https://www.linkedin.com/in/sandra-saluti-6866a686/
🔗 Related Links
* Sandra’s Blog - https://agderinthe.cloud/author/sandra/
📗 Chapters
00:00 Welcome to Entra Chat
03:18 Explaining Identity Governance
08:51 Handling Late Hires and Rehires
11:25 Using Directory Extensions Effectively
18:50 Stop Targeting UPNs for Automation
25:18 Managing Chaos with Guest Access Reviews
30:56 Deciding Who Approves App Access
33:51 Replacing Nested Groups with Access Packages
39:29 Closing Thoughts and Community
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeStop Leaving the Door Open: The Entra ID Hardening Checklist Security Experts Actually Use
Microsoft Entra security is evolving and the way organizations think about identity protection needs to evolve with it. In this episode, I’m joined by Sean Metcalf, one of the foremost identity security experts …
Shownotes
Microsoft Entra security is evolving and the way organizations think about identity protection needs to evolve with it. In this episode, I’m joined by Sean Metcalf, one of the foremost identity security experts in the industry, whose work has helped shape how many organizations approach securing both Active Directory and Microsoft Entra.Sean shares the hardening steps many teams still overlook, and why advances in AI are making it easier for both defenders and attackers to work faster than ever before. From MFA and application controls to protecting privileged accounts and reducing unnecessary exposure, this conversation offers a practical look at where strong identity security starts and why getting the fundamentals right matters more than ever.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Sean Metcalf
Sean Metcalf is the Identity Security Architect at TrustedSec and a renowned expert in Microsoft identity security. He holds the rare Certified Master in Active Directory certification and has spoken at major security conferences including Black Hat, DEF CON, and BlueHat on how to defend cloud and hybrid environments.
LinkedIn - https://www.linkedin.com/in/seanmmetcalf/
🔗 Related Links
* Securing Entra ID Administration: Tier 0 - https://trustedsec.com/blog/securing-entra-id-administration-tier-0
* Managing Privileged Roles in Microsoft Entra ID: A Pragmatic Approach - https://trustedsec.com/blog/managing-privileged-roles-in-microsoft-entra-id-a-pragmatic-approach
* Improve Entra ID Security More Quickly - https://adsecurity.org/?p=4825
* Microsoft Graph Skill - https://graph.pm
📗 Chapters
00:04:05 AI and the Evolution of Attacks
00:06:42 The Importance of Hardening Fundamentals
00:12:03 Securing Entra ID Quickly
00:16:24 Protecting Tokens with VBS and TPM
00:19:58 Restricting Consent and Guest Users
00:23:40 Managing Rogue Tenants
00:27:36 Cloud Admin Workstation Strategies
00:34:14 Delegated Admin Privileges
00:44:32 The Danger of Application Permissions
00:57:06 Artemis Mission Trivia
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Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribeHow to Design Bullet-Proof Conditional Access Policies in Microsoft Entra ID
If you can’t immediately name your break glass accounts and the last time you tested them → you’re already at risk.In this episode of Entra Chat, Microsoft MVP Per Torben walks through the conditional access …
Shownotes
If you can’t immediately name your break glass accounts and the last time you tested them → you’re already at risk.
In this episode of Entra Chat, Microsoft MVP Per Torben walks through the conditional access mistakes he sees even large enterprises making, and the practical framework he actually uses with customers.
You’ll learn how to set up emergency access accounts the right way, why your CA policies should be built more like a firewall than a checklist, and the one naming convention that makes managing dozens of policies actually manageable.
🎧 Hit play, your tenant will thank you.
Sponsored by:
Entra ID Gaps That Cause Outages
In Microsoft Entra ID, outages often start small: an expired client secret, a lapsed certificate, or a suddenly failing integration. Traditional controls don’t track credential expiry or enforce application ownership, so issues appear only after something breaks.
Teams are left asking:
* Which applications can access Microsoft 365 data?
* Is that access still appropriate?
* Who owns the app?
Unclear answers stall reviews, weaken accountability, and slow delivery.
ENow App Governance Accelerator closes these gaps by highlighting expiring credentials, surfacing permission risks, and identifying ownership gaps before they disrupt operations. New Standard Tier pricing makes it accessible for organizations under 10,000 users, typically $3,500–$9,500 annually.
Subscribe with your favorite podcast player or watch on YouTube 👇
About Per Torben
Per Torben is a Senior Architect at Crayon and a Microsoft MVP for Identity and Access. Based in Norway, he frequently writes highly-read posts featured on Entra.News and runs the collaborative tech blog “Agder in the Cloud”.
LinkedIn - https://www.linkedin.com/in/pertorbensorensen/
🔗 Related Links
* Agder in the Cloud - https://agderinthe.cloud
* I.D.E.A. for creating/configuring break-glass accounts
* GitHub - https://github.com/Per-Torben/I.D.E.A.
* Blog - https://agderinthe.cloud/2026/01/06/introducing-i-d-e-a-and-i-d-e-a-001/
* Protected actions: https://agderinthe.cloud/2025/02/12/protected-actions-adding-extra-guards-to-your-entra-id-gate/
* Conditional Access hardeing (series): https://agderinthe.cloud/2024/12/05/how-to-fix-the-fundamental-flaw-in-conditional-access-part-1-introduction-and-coverage-gapsCA geo filter (series): https://agderinthe.cloud/2025/11/06/diving-into-geo-filter-with-entra-conditional-access-part-1
* Entra Backup - https://learn.microsoft.com/en-us/entra/identity/role-based-access-control/backup-restore
📗 Chapters
06:22 The importance of Break Glass accounts
09:02 Securing emergency access with FIDO2 and RMAUs
18:10 Configuring Conditional Access: The “Block by Default” strategy
27:26 Managing scope and preventing accidental lockouts
29:31 Persona-based naming conventions for CA policies
35:38 Grouping settings and avoiding bloated policies
41:54 Handling exceptions and travel access with Access Packages
44:55 The flaw in Protected Actions for Conditional Access
53:38 Using the new Entra Backup feature for quick restores
Podcast Apps
🎙️ Entra.Chat - https://entra.chat
🎧 Apple Podcast → https://entra.chat/apple
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🎧 Overcast → https://entra.chat/overcast
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🎧 Others → https://entra.chat/rss
Merill’s socials
📺 YouTube → youtube.com/@merillx
👔 LinkedIn → linkedin.com/in/merill
🐤 Twitter → twitter.com/merill
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🐘 Mastodon → infosec.exchange/@merill
🧵 Threads → threads.net/@merillf
🤖 GitHub → github.com/merill
Get full access to Entra.News - Your weekly dose of Microsoft Entra at entra.news/subscribe
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