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Microsoft authentication issues can be frustrating because most of the time, the real problem is hidden behind generic error messages. In this video, we go deep into how to trace and analyze Microsoft authentication traffic using Fiddler, giving you full visibility into what actually happens during a sign-in attempt. You’ll learn how Fiddler captures HTTP and HTTPS authentication requests between Microsoft 365 Apps, Microsoft Entra ID (Azure AD), and Microsoft login endpoints. We’ll break down real authentication flows and show you how to identify where sign-in failures occur—whether it’s token issuance, conditional access evaluation, device registration checks, or unexpected redirects. This session covers how to: Capture Microsoft authentication traffic securely using Fiddler Understand sign-in request and response patterns from Microsoft endpoints Identify authentication failures that are not visible in Entra ID sign-in logs Correlate Fiddler traces with Microsoft error codes and authentication stages Troubleshoot complex login, activation, and verification issues using real network data This video is ideal for Microsoft 365 administrators, Entra ID engineers, IT support teams, and security professionals who want to move beyond guesswork and start troubleshooting authentication issues with real packet-level evidence. If you work with Microsoft cloud identities and want to understand what’s really happening during authentication, Fiddler is one of the most powerful tools you can add to your troubleshooting toolkit. #microsoft365 #fiddler #mfa #troubleshooting #entraid #itsupport #techguide #sysadmin #azure #azurelearning #microsoft #microsoftlearn