The fix works, 1.18.0-6ubuntu14.4 in Jammy fixes the bug. I've created the jammy container using steps from the [Test Plan] section listed above in the Bug Description. Then I installed nginx: $ apt install -y nginx and inside that container I typed in: $ apt policy nginx The output: nginx: Installed: 1.18.0-6ubuntu14.3 Candidate: 1.18.0-6ubuntu14.3 Version table: *** 1.18.0-6ubuntu14.3 500 500 http://archive.ubuntu.com/ubuntu jammy-updates/main amd64 Packages 500 http://security.ubuntu.com/ubuntu jammy-security/main amd64 Packages 100 /var/lib/dpkg/status 1.18.0-6ubuntu14 500 500 http://archive.ubuntu.com/ubuntu jammy/main amd64 Packages Then I repeated the steps from the [Test Plan] section. I've noticed that nothing has changed there, so the problem still exists: × nginx.service - A high performance web server and a reverse proxy server Loaded: loaded (/lib/systemd/system/nginx.service; enabled; vendor preset: enabled) Drop-In: /run/systemd/system/service.d └─zzz-lxc-service.conf Active: failed (Result: exit-code) since Wed 2023-06-28 19:03:05 UTC; 56s ago Docs: man:nginx(8) Process: 894 ExecStartPre=/usr/sbin/nginx -t -q -g daemon on; master_process on; (code=exited, status=0/SUCCESS) Process: 895 ExecStart=/usr/sbin/nginx -g daemon on; master_process on; (code=exited, status=1/FAILURE) Jun 28 19:03:05 jammy-test systemd[1]: Starting A high performance web server and a reverse proxy server... Jun 28 19:03:05 jammy-test nginx[895]: nginx: [emerg] bind() to unix:/run/serve-files.socket failed (98: Unknown error) Jun 28 19:03:05 jammy-test nginx[895]: nginx: [emerg] bind() to unix:/run/serve-files.socket failed (98: Unknown error) Jun 28 19:03:05 jammy-test nginx[895]: nginx: [emerg] bind() to unix:/run/serve-files.socket failed (98: Unknown error) Jun 28 19:03:05 jammy-test nginx[895]: nginx: [emerg] bind() to unix:/run/serve-files.socket failed (98: Unknown error) Jun 28 19:03:05 jammy-test nginx[895]: nginx: [emerg] bind() to unix:/run/serve-files.socket failed (98: Unknown error) Jun 28 19:03:05 jammy-test nginx[895]: nginx: [emerg] still could not bind() Jun 28 19:03:05 jammy-test systemd[1]: nginx.service: Control process exited, code=exited, status=1/FAILURE Jun 28 19:03:05 jammy-test systemd[1]: nginx.service: Failed with result 'exit-code'. Jun 28 19:03:05 jammy-test systemd[1]: Failed to start A high performance web server and a reverse proxy server. The nginx fails to upgrade, because the former issue that is caused makes the service non-startable and the upgrade will trigger a service restart in postinst. Since that fails it cannot upgrade - as expected. It has already been discussed in the comments above. Then, I just removed the offending socket file and restarted the service. Then I've upgraded nginx using: $ apt install nginx=1.18.0-6ubuntu14.4 Later I've typed in: $ apt policy nginx to check if the installed version has changed, and we see that we have a new version installed (with a fix). nginx: Installed: 1.18.0-6ubuntu14.4 Candidate: 1.18.0-6ubuntu14.4 Version table: *** 1.18.0-6ubuntu14.4 500 500 http://archive.ubuntu.com/ubuntu jammy-proposed/main amd64 Packages 100 /var/lib/dpkg/status 1.18.0-6ubuntu14.3 500 500 http://archive.ubuntu.com/ubuntu jammy-updates/main amd64 Packages 500 http://security.ubuntu.com/ubuntu jammy-security/main amd64 Packages Finally when I repeated steps from the [Test Plan] the problem did not exist, so the fix works. No error logs and nginx service works correctly.