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 Touch seeded packages, which is subscribed to systemd in Ubuntu. https://bugs.launchpad.net/bugs/1827286 Title: autofs - "Too many levels of symbolic links" after apt upgrade Status in autofs5 package in Ubuntu: New Bug description: Description: Ubuntu 16.04.6 LTS Release: 16.04 I moved to autofs this week as a workaround for Bug #1577575 failing to mount NFS entries at boot. This worked file until I ran 'apt upgrade' today. Now trying to access /vol/home mount results in the following error: root@chi:~# ls -la /vol/home/ ls: cannot access '/vol/home/': Too many levels of symbolic links root@chi:~# Oddly enough, the other two autofs entries work fine (output trimmed): root@chi:~# ls -la /vol/media total 4 ... root@chi:~# root@chi:~# ls -al /vol/temp/ total 24 ... root@chi:~# I have a scratch VM I can break tonight by performing upgrades individually and testing after each. Will provide that detail when available. Here is /var/log/apt/history.log Start-Date: 2019-05-01 17:37:00 Commandline: apt upgrade Upgrade: libdns-export162:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), libisccfg140:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), ureadahead:amd64 (0.100.0-19, 0.100.0-19.1), libldap-2.4-2:amd64 (2.4.42+dfsg-2ubuntu3.4, 2.4.42+dfsg-2ubuntu3.5), libirs141:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), bind9-host:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), dnsutils:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), libisc160:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), passwd:amd64 (1:4.2-3.1ubuntu5.3, 1:4.2-3.1ubuntu5.4), bind9utils:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), libisc-export160:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), liblwres141:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), login:amd64 (1:4.2-3.1ubuntu5.3, 1:4.2-3.1ubuntu5.4), iproute2:amd64 (4.3.0-1ubuntu3.16.04.4, 4.3.0-1ubuntu3.16.04.5), bind9:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), libdns162:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), unattended-upgrades:amd64 (0.90ubuntu0.10, 1.1ubuntu1.18.04.7~16.04.2), libisccc140:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), libbind9-140:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), uidmap:amd64 (1:4.2-3.1ubuntu5.3, 1:4.2-3.1ubuntu5.4), bind9-doc:amd64 (1:9.10.3.dfsg.P4-8ubuntu1.12, 1:9.10.3.dfsg.P4-8ubuntu1.14), tzdata:amd64 (2018i-0ubuntu0.16.04, 2019a-0ubuntu0.16.04) End-Date: 2019-05-01 17:37:24 To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/autofs5/+bug/1827286/+subscriptions -- Mailing list: https://launchpad.net/~touch-packages Post to : touch-packages@lists.launchpad.net Unsubscribe : https://launchpad.net/~touch-packages More help : https://help.launchpad.net/ListHelp