Hi DaBigKahuna,
Sometimes Outlook users with large mailboxes are more likely to encounter some problems.
I suggest you check to see whether the problem is caused by damaged Outlook preferences.
You can refer to step 4 in the article below:
http://support.microsoft.com/kb/2409331
If the issue persists after finishing the step above, this issue may be related to Outlook 2011 for Mac.
To help us improve our products, I recommend you post the issue with detailed information in our Outlook 2011 for Mac Forum:
http://www.microsoft.com/mac/support
Thanks for feedback regarding the issue. Your understanding is appreciated.
Best Regards,
Chris Ni