Today I want to walk through how to configure Azure App Service Authentication when your App Service sits behind Azure Front Door and is accessed through a Private Link. On a dreadful day in october 2025, I received something that most IT people fear - a request from a client! The request included information from the client, that they were struggling with authentication on a Web App deployed behind Azure Front Door using Private Link. What looked like a straightforward setup

We’ve covered what Authentication Contexts are, why they matter, and how they help us strengthen access and data security in Microsoft 365. Now it’s time to answer the next question - how do we monitor and report on their usage? Unfortunately, there’s no built-in way to gain that visibility today. Neither Entra ID nor Microsoft 365 provides a simple method to inventory or audit Authentication Contexts across our estate including Conditional Access, PIM and Sensitivity labels

With identities and access strengthened in part 2 , it’s time to turn our focus to real-world data protection  with Authentication Contexts. One of the more underused capabilities of Authentication Contexts is their power to secure data across the environment, whether through direct enforcement using Sensitivity Labels or by protecting user sessions via Microsoft Defender for Cloud Apps. In this post, we’ll explore exactly that: how to secure organizational data using Authent

In Part 1 of this mini-series, we explored the what, why, and how of Microsoft Entra Authentication Contexts, laying the foundation for what they are and how they work. In this second part, we’ll build on that foundation with real-world examples of how Authentication Contexts can secure user access and critical actions. Along the way, we’ll walk through configurations, share recommendations, and look at the Conditional Access policies that tie it all together. So, let’s dive

Over my last few posts, I’ve casually mentioned Authentication Context a few times, so I thought it was about time we gave the feature a proper spotlight. Within Microsoft Entra, we sometimes encounter scenarios where we need to enforce specific conditions for certain sub-actions or unique requirements. While Conditional Access can directly enforce conditions in most cases, there are times when it’s trickier — especially if we want to enforce a condition for a single  action

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