One of our customers recently started having this issue whereby all Terminal Server users were getting the following prompt when opening Outlook;
Outlook failed to start correctly last time. Starting Outlook in safe mode
will help you correct or isolate a startup problem in order to successfully
start the program. Some functionality may be disabled in this mode.
Do you want to start Outlook in safe mode?
Whether they chose Yes or No they still got the prompt the next time they opened Outlook.
After a lot of research I found out that a registry key on the Terminal Server needs deleting in order to fix this issue, the key is below;
Deleting HKLMSoftwareMicrosoftWindows NTCurrent VersionTerminal ServerInstallSoftwareMicrosoftOffice10.0OutlookResiliency