Hi Layne,
I understand you encounter an issue that need to reactive the Outlook for Mac every time when restarting it. I would like to confirm if you have tried un-installing an re-installing it?
If the issue still exists after doing that, I suggest un-installing the Outlook for Mac> removing those files listed below>re-installing the Outlook for Mac to see whether the issue will exists. As some of customers who encounter the re-activating for Outlook for Mac issues can resolve the issue using this way: http://community.office365.com/themes/groups/generic/forums/thread.aspx?ForumID=172&ForumThreadID=287148&GroupKeys=en-us/
- ~/Library/Group Containers/U*
- ~/Library/Caches/com.microsoft.Outlook
- ~/Library/Containers/com.microsoft.Outlook
Let me know any updates of the issue at your convenience.
Thanks,
Iris He