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Shutting Down/Rebooting Debian/Ubuntu/Mint

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I administer a Linux Mint system remotely. Sometimes I need to reboot the system, but have difficulty with the shutdown command. I usually use shutdown -r "now" to reboot. The system starts to reboot but ends up either hanging or giving a message to login to root in maintenance mode or press ctrl+d.

This ends up requiring someone on site to manually reboot it. I've noticed this with Debian as well. Am I doing something wrong. I want to be able to remotely reboot the system without the need for anyone to physically reboot the server locally.

Thanks


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