I think I found a relevant upstream bug [0], fixed by [1]. If the patch applies fairly cleanly to the version in Focal this could be good SRU material.
[0] https://bugzilla.mindrot.org/show_bug.cgi?id=3122 [1] https://github.com/openssh/openssh-portable/commit/7af1e92cd289b7eaa9a683e9a6f2fddd98f37a01 ** Changed in: openssh (Ubuntu Focal) Status: Confirmed => Triaged ** Bug watch added: OpenSSH Portable Bugzilla #3122 https://bugzilla.mindrot.org/show_bug.cgi?id=3122 ** Also affects: openssh via https://bugzilla.mindrot.org/show_bug.cgi?id=3122 Importance: Unknown Status: Unknown -- 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 portable OpenSSH: Unknown Status in openssh package in Ubuntu: Fix Released Status in openssh source package in Focal: Triaged 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/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