I'm really frustrated, I'm not an Apple fanboy, I like Windows I like Apple, I actually don't like Linux.. but more importantly I understand they're all tools to achieve different ends. I need to qualify that because otherwise my next statement will sounds like typical fanboy rhetoric. All platitudes aside, Outlook 2011 is the only program I run that consistently crashes on my Mac. I run Outlook 2010 and 2013 on my VMs and it's a great piece of software, I will argue anyone that it is the best email client. However I don't know why MS can't replicate the success on Mac I've tried Entourage, and now Outlook 2011 and both are colossal heaps of ****. They're gaudy and over complicated in places that should be simple, while somehow being too simplistic in places that should have more options. I don't understand why they couldn't just port 2010 over, give it an Apple facelift.... I'm sorry, as I said I'm just frustrated and I want my sentiments on record somewhere for all eternity on the matter.

NOW..

The problem at hand. I can usually recover from any crashes or hiccups, however I can't get past this issue with my Exchange mail. I've got a IMAP account and I'm migrating it to Exchange. I moved one of my folders in Outlook that was under the IMAP account to the Exchange account. Outlook started to push the mail up to the server and but then stopped with 400 messages remaining. I've tried rebooting, installing updates, I even contacted the Office 365 support (where my Exchange account is hosted) they determined the issue was local to Outlook and not the server. I'm an IT professional, so I do understand a little about this kinda stuff and I'm trying to avoid the whole nuke the program and reinstall option which seems to be everyones go to move with hard problems. Perhaps that may be solution, but I'm looking for other alternatives in the meantime. If anyone can assist me please let me know what information you need from me, specs are below.

Microsoft Outlook for Mac 2011 Version 14.3.9 - OS X Mavericks 10.9.2