Can’t remote login after startup

restartscreen-sharingsleep-wakessh

I have an iMac running Catalina (10.15.2) that I don't have a keyboard or mouse plugged into. I just want to use it via screen sharing and SSH.

The problem is that often when I want to use it I can't. SSH hangs, screen sharing won't connect. I've tried restarting it via the power button, but even when it gets to the login screen I can't use SSH or screen sharing.

The only thing that seems to work is plugging in a keyboard and mouse, and logging in the normal way. Then SSH and screen sharing start working. They continue to work for a while. Eventually I come back and it's back in a bad state.

In Energy Saver settings I checked "Prevent computer from sleeping" and "Wake for network access" as well as "Start up automatically after power failure", power nap and hard disk sleep are unchecked.

Best Answer

This is caused by having FileVault enabled in the security settings. The disk won't decrypt until someone logs in, so services like remote desktop and sshd won't start until then.