Description

Mike Soule, Field CTO at Sentinel Technologies, returns to the PowerShell Podcast for the first time in three years to talk identity security, cloud configuration testing, and the evolving role of AI in the Microsoft ecosystem. Andrew and Mike dig into Maester, the open source PowerShell-based test automation framework that applies unit testing concepts to Microsoft 365 security configuration. Mike breaks down how Maester works, how Sentinel uses it with clients, and how the community has grown it into something that spans hundreds of built-in tests covering conditional access, CIS baselines, CISA standards, and more. They also cover EntraOps, the Enterprise Access Model, AI's impact on the MSP world, and why working in managed services is still one of the fastest ways to level up in IT. The episode closes with a strong Brandon Sanderson tangent.

Key Takeaways:

• Maester brings the concept of unit testing to Microsoft 365 security configuration, letting admins continuously validate their cloud settings against known-good baselines with as few as three PowerShell commands. It's built on Pester, is fully open source, and now has over 100 community contributors.
• AI is changing the MSP landscape fast, but the fundamentals still matter. Mike and Andrew discuss how to think about Copilot licensing complexity, model routing in agent stacks, and why meeting users in their existing interface is often more important than deploying a shiny new tool.
• MSP experience accelerates learning in a way that internal IT often can't match. When you're working across multiple clients and environments, you accumulate reps quickly, and that breadth is hard to replicate elsewhere.

Guest Bio:
Mike Soule is the Field CTO at Sentinel Technologies, a large managed service provider focused on identity, cloud, and security strategy. Mike has been working hands-on with PowerShell, Entra ID, and Microsoft 365 security architecture for years and is a regular speaker at identity and security conferences.

Resource Links:
Maester (open source framework): https://maester.dev
Maester on GitHub: https://github.com/maester365/maester
Maester Cloud (hosted version by Merill Fernando): https://maester.cloud
HIPConf (Hybrid Identity Protection Conference): https://www.hipconf.com
EntraOps by Thomas Naunheim: https://github.com/Cloud-Architekt/EntraOps
Mike Soule on LinkedIn: https://www.linkedin.com/in/mikesoule
The PowerShell Podcast on YouTube: https://youtu.be/EQK693gGWoo