Looks like the issue is symlinking to a director prior to autofs mounting it.
Everything fine... root@numbersix:/# ssh chi uname -a Linux chi 4.4.0-146-generic #172-Ubuntu SMP Wed Apr 3 09:00:08 UTC 2019 x86_64 x86_64 x86_64 GNU/Linux root@chi:~# ls -la /home ls: cannot access '/home': No such file or directory root@chi:~# root@numbersix:/# ssh chi 'ls -la /vol/*' /vol/home: total 8 drwxr-xr-x 1 root root 154 Apr 21 19:10 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. drwxr-xr-x 1 2005 2005 1070 Nov 17 2015 bethann [trimmed] /vol/media: total 4 drwxr-xr-x 1 root root 128 Apr 13 18:29 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. [trimmed] /vol/zhora-temp: total 24 dr-xr-xr-x 6 root root 4096 Mar 3 08:21 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. [trimmed] root@numbersix:/# Everything works fine if the link is made after... root@chi:/# ln -s /vol/home root@chi:/# ls -la /home lrwxrwxrwx 1 root root 9 May 2 12:11 /home -> /vol/home root@chi:/# root@chi:/# ls -la /vol/* /vol/home: total 8 drwxr-xr-x 1 root root 154 Apr 21 19:10 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. [trimmed] /vol/media: total 4 drwxr-xr-x 1 root root 128 Apr 13 18:29 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. [trimmed] /vol/zhora-temp: total 24 dr-xr-xr-x 6 root root 4096 Mar 3 08:21 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. [trimmed] root@chi:/# It breaks after the reboot... root@chi:/# init 6 Connection to chi closed by remote host. Connection to chi closed. root@numbersix:~# root@chi:/# init 6 Connection to chi closed by remote host. Connection to chi closed. root@numbersix:~# root@numbersix:~# root@numbersix:~# ssh chi Welcome to Ubuntu 16.04.6 LTS (GNU/Linux 4.4.0-146-generic x86_64) * Documentation: https://help.ubuntu.com * Management: https://landscape.canonical.com * Support: https://ubuntu.com/advantage 21 packages can be updated. 15 updates are security updates. New release '18.04.2 LTS' available. Run 'do-release-upgrade' to upgrade to it. root@chi:~# ls -la /vol/* ls: cannot open directory '/vol/home': Too many levels of symbolic links /vol/media: total 4 drwxr-xr-x 1 root root 128 Apr 13 18:29 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. [trimmed] /vol/zhora-temp: total 24 dr-xr-xr-x 6 root root 4096 Mar 3 08:21 . drwxr-xr-x 5 root root 4096 Jul 2 2018 .. [trimmed] root@chi:~# At this point, the link needs to be deleted and the VM rebooted to get back to a normal state - just restarting autofs won't clear it. ** Package changed: systemd (Ubuntu) => autofs5 (Ubuntu) -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1827286 Title: autofs - "Too many levels of symbolic links" after apt upgrade To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/autofs5/+bug/1827286/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs