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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