I'm having an issue with an Outlook plugin that keeps asking for SSO credentials after the first successful login. When a user clicks on the plugin, they are directed to Azure AD for authentication, which works initially. However, after that, every time they try to use the plugin again, it prompts them for their credentials instead of keeping them logged in. I've ruled out any Conditional Access Policies being the cause. Could the problem be related to a private WebView being used by the plugin? Any help or advice would be appreciated as this is causing delays for users.
2 Answers
It sounds like the issue might be with the plugin using an embedded browser instead of the actual system browser. Private WebView sessions can break SSO persistence. If you switch to Edge WebView2, it could resolve the problem. Do you know how to make that change in your setup?
Have you checked if the subsequent logins actually go through? Sometimes they might still work even if you’re seeing the prompt again.

I noticed the same issue with the web version of Outlook too. Any tips on how to switch to Edge WebView2 from the current setup?