Having recently had a very random issue in a school I thought I'd post it up.
When closing Outlook 2010 the application crashes and asks if you would like to restart it every time. An application event log message is written however has no useful information within it.
Disabling all Add-ins and running the application as a Domain Admin has no effect.
It turns out that it was caused by the following Group Policy Object setting. How odd. I hope this is enough information for someone to find this thread if they get stuck with the same randomness!
User Configuration GPO
Microsoft Outlook 2010/Disable Items in User Interface/Predefined/Disable Quick Steps Gallery
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