Had a weird issue on my MacMini, with macOS 10.15.7 Catalina. I wanted to enable remote login on the machine, which I know for a fact was once working. Today however, all I got was this:
After enabling it for one or multiple users, the SSH service appears to try to start, but never gets going so remote logins aren’t possible. Turns out this “feature” has been introduced after the latest security patches from what I understand, and it being a legacy OS, it’ll likely never see a fix.
Thankfully there is a temporary fix that has to be applied after each restart, but it does cure the problem. Open a Terminal session and type this:
sudo launchctl load -w /System/Library/LaunchDaemons/ssh.plist
Pretty much instantly, remote login switches to “on”. Huzzah!
Thanks to xinlino for this solution!