Mastering Microsoft Entra ID: Real-World Passkey Deployment Tips

January 31, 2026 · 46 min

Show notes

In this episode, we sit down with Eric Woodruff, Chief Identity Architect at Semperis, to discuss the reality of achieving a 100% phishing-resistant environment. Over the course of just three months, Eric led a 600-person organization through a complete rollout of passkeys, Windows Hello for Business, and Platform SSO. This conversation moves beyond the technical “knobs and dials” to explore why organizational change management and C-suite buy-in are the true foundations of a successful identity modernization project.

Eric shares the creative strategies his team used to drive adoption, including a custom self-enrollment portal built with Power Platform that allowed early adopters to “dogfood” the technology. We dive into the “voluntold” phase of the rollout, where voluntary participation transitioned into mandatory policy, and how they used Power BI to track progress and identify “stragglers”. The episode also provides a transparent look at the technical hurdles encountered, from legacy application exclusions to troubleshooting older Android devices and niche browsers.

Looking ahead, we discuss the critical importance of protecting against “downgrade attacks,” where sophisticated phishing attempts try to bypass modern security by tricking users into traditional password entries. Eric emphasizes that the final mile of this journey—removing passwords entirely—is as much about supporting your helpdesk and documenting processes as it is about the technology itself. Whether you are managing a cloud-only tenant or navigating complex hybrid scenarios, this episode offers a practical roadmap for the future of enterprise identity.

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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/

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📗 Chapters

02:50 Rolling Out Passkeys

06:47 Application and Device Issues

09:49 Identifying Password Users

12:15 Lessons Learned for 2026

15:14 Understanding Downgrade Attacks

20:10 The NoAuth Vulnerability