Outlook Not Asking for Password After Changing Password: A Baffling Issue

As IT administrators, we often encounter issues that seem to defy explanation. One such problem is when Outlook refuses to prompt users for their password after changing it. This phenomenon has left many users scratching their heads, wondering what could be causing this strange behavior.

In our case, we have implemented a Smoothwall UTM in place with port forwarding and firewall rules to allow mail traffic between our on-premise Exchange environment and Office 365. Our users' email addresses and userPrincipalName match, which makes it challenging to pinpoint the root cause of the issue. We are currently running Exchange 2013 with Office 2016, and we have set up a hybrid environment with O365 for mail filtering.

The problem occurs only once, after the first login to Windows 10. It's as if Outlook is not recognizing the changed password or has lost its connection. Our users report that they receive no login prompts when launching Outlook 2016, which makes it difficult for them to access their email accounts.

We have also implemented Azure AD Connect on the same box with SSO to O365 enabled, but this does not seem to be resolving the issue. The problem persists despite our best efforts to troubleshoot and resolve the issue.

If you or someone in your organization is experiencing a similar issue, we would love to hear from you. Have you encountered this problem before? How did you manage to resolve it? Your insights could help us better understand what's going on behind the scenes and find a solution to this baffling issue.

Outlook not asking for password after changing password