Hi Pinbot,
Thanks for the update information.
Based on the current situation, I would suggest you clear the cache of the folders in Outlook 2011:
1. Start Outlook 2011.
2. Right-click or Control-click on a folder, select Folder properties, click Empty.
Additionally, to find out the root cause of the issue, I recommend you turn logging on in Outlook 2011. See Turn logging on or off in Outlook for Mac 2011. Considering that it could contain private information, I have sent you a private message to require the log. Therefore you can reply the private message with the detailed log information.
Here are the steps to access the private message :
1. Please go to the Your details section on the right side of the community site.
2. Click Private messages.
3. Click the subject title of the response to read the message and reply with your information.
Moreover, you can post the issue in our dedicated Outlook for Mac Forum. Our engineers in that forum are more familiar with Outlook for Mac.
I will keep monitoring any updates on the issue to help you.
@David,
You can try these steps as well. And I have sent you a private message too.
Best Regards,
Bruce Zhou