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When I reboot a headless Mac Mini server running macOS Mojave with sudo reboot, it becomes non-ssh-able. The same happens if a "fake monitor" HDMI display emulator is plugged in. This happens consistently with multiple Mac Mini machines. Interestingly, a "hard reboot" (holding the power button until the machine switches off, and then turning it on again) allows the host to come back online, even without plugging in a monitor.

Also, this issue does not happen if a real monitor is plugged in -- in this case the machine reboots fine and comes back online.

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The obvious thing to check is if you have FileVault enabled and attach a display simulator dongle. In the FileVault case, the machine does not restart to the OS but to a firmware / limited log in screen, but having a display connected won’t enable/disable FileVault.

You will want to have a remote KVM or someone that can log in for unexpected power failures. See this thread for a lot more options like power, display and management options for headless Macs.

Removing FileVault would allow the OS to boot fully in exchange for the data not being encrypted at rest.

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  • I have a Mac mini M1 without attached display, keyboard, and mouse, but only LAN and power plug. I also met the ssh and Chrome Remote Desktop problem after rebooting macOS. Fortunately, I work around the problem by disabling FileVault!
    – Meng-Yuan Huang
    Commented Dec 15, 2022 at 1:02
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    Good point @Meng-YuanHuang I should edit that in as something explicitly to try in the post above.
    – bmike ♦
    Commented Dec 15, 2022 at 1:05

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