This reminds me of several previous bugs; this may or may not be a duplicate, and this may or may not be intentional behaviour. Hopefully these are are useful and save some debugging effort:
https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1922212 https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1876320 https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1873528 Especially 1873528 feels like most likely to be relevant, I suggesting reading that one first. Thanks -- You received this bug notification because you are a member of Ubuntu Bugs, which is subscribed to Ubuntu. https://bugs.launchpad.net/bugs/1968305 Title: sshd_config.d overrides not working To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/1968305/+subscriptions -- ubuntu-bugs mailing list ubuntu-bugs@lists.ubuntu.com https://lists.ubuntu.com/mailman/listinfo/ubuntu-bugs