Maester and Overe both help with Conditional Access security in Microsoft 365 — but they solve different problems. Here is when to use each, and why testing is not the same as assurance.
Conditional Access is one of the most important controls in Microsoft 365. It decides who can access what, from where, on what device, and under which conditions.
The problem is not that most teams have no Conditional Access policies. Most do. The problem is proving those policies are actually working the way everyone thinks they are.
That is where Maester and Overe both become relevant — but they solve different problems.
Maester is an open-source framework for Microsoft 365 security testing. It helps technical teams run repeatable checks, validate known scenarios, and bring security-as-code practices into their Microsoft 365 environment.
Overe is built for Conditional Access Assurance. It helps teams find hidden gaps, bypass paths, risky exclusions, and policy combinations that leave access exposed — even when the tenant looks secure on paper.
Maester helps you test what you already know to check. Overe helps you find the Conditional Access gaps you didn't know existed.
Conditional Access gets complicated quickly. A tenant might have policies covering MFA, admin accounts, device compliance, legacy authentication, guest access, named locations, and sensitive apps. On paper, that can look strong.
But things change. Users move groups. Apps get added. Exclusions build up. Emergency access accounts sit outside normal controls. A small exception that made sense six months ago quietly becomes a real exposure — and no Microsoft-native alert fires when it happens.
Testing known scenarios is useful. But if you know exactly what to test, you can only find the problems you already suspected.
The harder question is: what are we missing?
That is the question Overe is built to answer.
