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Is there any way to force Windows to reboot itself remotely when rdesktop fails completely? I can't get it to accept any form of key combination or at a minimum, it is unresponsive to ctrl+shift+end/del/win+b/etc. I'm using a Microsoft account so psexec is a no go.

rdesktop accepts my credentials and begins logging on, but then ends with the standard "Your Remote Desktop Session has ended..."

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It seems something breaks during the login itself. Microsoft's rdesktop client uses Network Level Authentication (NLA) and pre-auths your creds before connecting to the session, but Linux's rdesktop does not.

On a hunch that something was happening with NLA/during the login sequence, I connected via rdesktop on Linux and it dropped me to the login screen. Interestingly, attempting to login still failed however, I was able to simply reboot the host with the power button on the login screen.

TLDR: Try rdesktop from Linux and see if it gets you the login splash screen and then reboot.