
Hi Lorenzo
Thanks for reaching out to Microsoft Q&A forum support
Based on your description, I understand that one user is experiencing recurring Outlook sync issues. Specifically, Outlook disconnects from the server during startup, shutdown, mail operations, and regular syncs, occurring 3 to 4 times daily. The issue requires a full PC restart to resolve, and while other Microsoft 365 apps function normally, Outlook remains unstable. You've already taken several troubleshooting steps, including repairing the profile, toggling cache mode, updating Outlook, and clearing cache and sync folders.
The challenge appears to be related to persistent background Outlook processes and failed reconnection attempts. Multiple instances of Outlook remain active in Task Manager even after closure, and the system tray displays a greyed-out Outlook icon attempting to reconnect.
This behavior suggests that Outlook may be hanging during shutdown or failing to release resources properly, which can interfere with subsequent launches and server connections. Since other users onsite are unaffected and OneDrive syncs without issue, the problem is likely isolated to the affected user's Outlook configuration or local environment.
As a first approach, I recommend launching Outlook in Safe Mode using the command Outlook.exe /safe
. This disables all add-ins and helps determine whether a third-party extension is causing the instability. If Outlook runs smoothly in Safe Mode, you can proceed with the following steps:
- Disable add-ins via File > Options > Add-ins > Manage COM Add-ins.
- Use the command
Outlook /rpcdiag
to open the Connection Status window and identify which service is failing.
Hope my answer will help you, for any further support, kindly let me know
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