Thanks for the update! I managed to reproduce this on my end: $ lxc launch images:ubuntu/focal test-ssh-focal $ lxc exec test-ssh-focal bash
# apt update && apt upgrade -y # apt install openssh-server # adduser user > ssh into container from another terminal to show pw auth is available by default: $ ssh user@<container-ip> user@<container-ip>'s password: > Update /etc/ssh/sshd_config with the following in first terminal Match User user PasswordAuthentication No Match All # systemctl restart sshd > Check again in other terminal $ ssh user@<container-ip> user@<container-ip>: Permission denied (publickey). > Now remove the lines from /etc/ssh/sshd_config and add them to /etc/ssh/sshd_config.d/username.conf # systemctl restart sshd > Check if the other config worked in other terminal (it does not) $ ssh user@<container-ip> user@<container-ip>'s password: I did, however, confirm this works for Jammy and Kinetic, so this is a Focal-specific issue. Marking as such ** Also affects: openssh (Ubuntu Focal) Importance: Undecided Status: New ** Changed in: openssh (Ubuntu) Status: Incomplete => Fix Released ** Changed in: openssh (Ubuntu Focal) Status: New => Confirmed ** Tags added: server-todo -- You received this bug notification because you are a member of Ubuntu Touch seeded packages, which is subscribed to openssh in Ubuntu. https://bugs.launchpad.net/bugs/2012298 Title: PasswordAuthenticaion in sshd_config.d Status in openssh package in Ubuntu: Fix Released Status in openssh source package in Focal: Confirmed Bug description: The stanza Match User <username> PasswordAuthentication no in /etc/ssh/sshd_config works as expected. The same stanza in /etc/ssh/sshd_config.d/username.conf does not work. The Include in /etc/ssh/sshd_config is not commented out, and /usr/sbin/sshd -D -ddd shows the username.config file being parsed. ProblemType: Bug DistroRelease: Ubuntu 20.04 Package: openssh-server 1:8.2p1-4ubuntu0.5 ProcVersionSignature: Ubuntu 5.4.0-131.147-generic 5.4.210 Uname: Linux 5.4.0-131-generic x86_64 NonfreeKernelModules: falcon_lsm_serviceable falcon_nf_netcontain falcon_kal falcon_lsm_pinned_14713 ApportVersion: 2.20.11-0ubuntu27.25 Architecture: amd64 CasperMD5CheckResult: skip Date: Mon Mar 20 13:34:14 2023 InstallationDate: Installed on 2022-11-04 (136 days ago) InstallationMedia: SSHDConfig: Error: command ['pkexec', '/usr/sbin/sshd', '-T'] failed with exit code 127: pkexec must be setuid root SourcePackage: openssh UpgradeStatus: No upgrade log present (probably fresh install) To manage notifications about this bug go to: https://bugs.launchpad.net/ubuntu/+source/openssh/+bug/2012298/+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