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From Okta to Entra: Migrating 700 Apps in 90 Days
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From Okta to Entra: Migrating 700 Apps in 90 Days

Ben Wolfe shares how his team executed an ambitious identity migration while implementing Windows Hello for Business—all with minimal user disruption.

Episode Summary

I'm thrilled to launch the first episode of Entra.Chat, my new podcast where we'll dive into all things Microsoft Entra! For my inaugural episode, I couldn't think of a better guest than Ben Wolfe, who heads security solutions at Increment and was actually my former manager at Microsoft.

In this episode, Ben and I explore his journey from the early days of Exchange to becoming an identity expert. Ben shares the fascinating story of how he led a massive migration project - moving 700 applications and 30,000 users from Okta to Microsoft Entra in just three months, all while implementing Windows Hello for Business simultaneously!

Chapter Headlines

00:00 - Introduction and Background

  • Merill introduces his first podcast guest, Ben Wolfe from Increment

  • Ben's history with Microsoft and transition from Exchange to cloud identity

06:45 - The Evolution from Exchange to Azure AD

  • Early days of Exchange and Active Directory integration

  • Transition to cloud solutions and identity challenges

14:30 - Enterprise Identity Challenges

  • How Azure AD solved enterprise identity problems

  • Comparing on-premises AD limitations to cloud capabilities

24:30 - Major Migration: Okta to Microsoft Entra

  • Strategy for migrating 700 apps and 30,000 users in three months

  • Implementing stage rollout and Windows Hello for Business simultaneously

33:45 - Technical Migration Challenges

  • Handling SAML claims and application-specific requirements

  • Using browser tools to troubleshoot authentication issues

41:50 - User Experience and Change Management

  • Minimizing help desk calls during migration

  • Pre-staging applications to maintain user experience

48:20 - Identity Governance Implementation

  • Using access packages for automated user entitlements

  • Working with dynamic groups and custom extensions

56:15 - Custom Claims and Access Management

  • Developing custom claims providers for complex requirements

  • Using Azure Functions to extend identity capabilities

01:00:45 - Wrap-Up and Final Thoughts

  • The value of community knowledge sharing

  • Invitation to reach out for identity management assistance

Key Insights

  • Stage rollout allows for gradual migration from federated identity providers to Microsoft Entra

  • Windows Hello for Business implementation can be combined with identity migration

  • Access packages in Identity Governance provide powerful automation of entitlements

  • Custom claims providers can solve complex authentication scenarios

  • SAML trace browser extensions significantly simplify troubleshooting

About Ben

Ben Wolfe heads the security solutions practice at Increment, a Microsoft partner in Australia. Previously, he worked at Microsoft where he was Merill's manager and has extensive experience with Microsoft Entra deployments and migrations.

Ben Wolfe - https://www.linkedin.com/in/benjaminwillwolfe/

Increment - https://www.increment.inc/

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