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Can’t upgrade Win 2003 + ISA 2006 to Windows 2008

Autor brendon

If you just happen to have an old VM running DC services for your house and it just happens to have ISA installed for testing but you happened to forget it was there. When upgrading the operating system to Windows Server 2008 it is going to fail with a CRITICAL_SERVICE_FAILED_TO_START error (0x0000005A) after the second reboot. Don’t panic, or trying to boot into safe mode to view the event log because that doesn’t work.

Simply restart and when presented an option for the version of windows to load, select the ‘Roll-back Windows Upgrade’ option. Un-install ISA from Windows 2003 and then attempt the upgrade again.

 I’m sure the upgrade how-to specified this as a step but it is much more fun learning by trial and error.