this particular occurrence was on windows 2008 sp2 (32-bit) and very easy to reproduce. every time the system was rebooted the VM would report vmware tools not running and sometimes vmware not running (not installed). RDP sessions would not function. when trying to login to the VM console it would hang on “applying user settings”.

this all started occurring after the system experienced a non-graceful shutdown. i ended up finding a vmware kb article that referenced a microsoft article.

the solution was to boot into safe mode and edit the registry:
HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Services\HTTP
Add DependOnService (multi-string value)
and set the value to CRYPTSVC

sources:
http://kb.vmware.com/selfservice/microsites/search.do?language=en_US&cmd=displayKC&externalId=2005330
http://support.microsoft.com/kb/2379016

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