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  1. The installer crashes if run within session 0, e.g. from a scheduled task or psexec -s. Interactive use as system works, e.g. psexec -s -i. To reproduce download the installer and psexec and run: psexec -s This will fail with SetupFrontEnd.exe causing an exception of some sort and crashing. The following will work fine: psexec -s -i Normally this wouldn't be much of a problem because it wouldn't be run that way, but running Chocolatey updates from a scheduled task will fail because of this and there isn't an easy way around that.