This type of delay trying to restart or shutdown often happens here on far more than a single installation. The instant case is 14.0.12 on host ab560 running Bullseye. Notable slices from journalctl -b -1:
Dec 14 20:55:56 ab560 systemd[1]: dev-hugepages.mount: Succeeded. Dec 14 20:55:56 ab560 systemd[1]: proc-sys-fs-binfmt_misc.automount: Got hangup/error on autofs pipe from kernel. Likely our automount point has been unmounted by someone or something else? Dec 14 20:55:56 ab560 systemd[1]: proc-sys-fs-binfmt_misc.automount: Failed with result 'unmounted'. Dec 14 20:55:56 ab560 systemd-logind[532]: System is rebooting. Dec 14 20:55:56 ab560 systemd[1]: Stopping Session 3 of user root. Dec 14 20:55:56 ab560 systemd[1]: Removed slice system-modprobe.slice. ... Dec 14 20:55:56 ab560 watchdog[773]: stopping daemon (5.16) Dec 14 20:55:56 ab560 systemd[1]: Stopping watchdog daemon... Dec 14 20:55:56 ab560 systemd[1]: nfs-blkmap.service: Main process exited, code=exited, status=1/FAILURE Dec 14 20:55:56 ab560 systemd[1]: nfs-blkmap.service: Failed with result 'exit-code'. Dec 14 20:55:56 ab560 systemd[1]: Stopped pNFS block layout mapping daemon. Dec 14 20:55:56 ab560 systemd[1]: session-3.scope: Succeeded. ... Dec 14 20:55:56 ab560 systemd[1]: Reached target Unmount All Filesystems. Dec 14 20:55:56 ab560 systemd[1]: user-runtime-dir@0.service: Succeeded. Dec 14 20:55:56 ab560 systemd[1]: Stopped User Runtime Directory /run/user/0. Dec 14 20:55:56 ab560 systemd[1]: Removed slice User Slice of UID 0. Dec 14 20:55:56 ab560 systemd[1]: user-0.slice: Consumed 10.876s CPU time. Dec 14 20:55:56 ab560 systemd[1]: watchdog.service: Control process exited, code=exited, status=1/FAILURE Dec 14 20:55:56 ab560 systemd[1]: watchdog.service: Failed with result 'exit-code'. Dec 14 20:55:56 ab560 systemd[1]: Stopped watchdog daemon. Dec 14 20:55:56 ab560 systemd[1]: watchdog.service: Triggering OnFailure= dependencies. Dec 14 20:55:56 ab560 systemd[1]: Requested transaction contradicts existing jobs: Transaction for wd_keepalive.service/start is destructive (systemd-sysctl.service has 'stop' job queued, > Dec 14 20:55:56 ab560 systemd[1]: watchdog.service: Failed to enqueue OnFailure= job, ignoring: Transaction for wd_keepalive.service/start is destructive (systemd-sysctl.service has 'stop'> Dec 14 20:55:56 ab560 systemd[1]: Stopped target Multi-User System. ... Dec 14 20:55:56 ab560 systemd[1]: smbd.service: Succeeded. Dec 14 20:55:56 ab560 systemd[1]: Stopped Samba SMB Daemon. Dec 14 20:55:56 ab560 nmbd[528]: [2021/12/14 20:55:56.728880, 0] ../../source3/nmbd/nmbd.c:59(terminate) Dec 14 20:55:56 ab560 nmbd[528]: Got SIGTERM: going down... Dec 14 20:55:56 ab560 systemd[1]: Stopping Samba NMB Daemon... Dec 14 20:55:56 ab560 systemd[1]: hddtemp.service: Succeeded. Dec 14 20:55:56 ab560 systemd[1]: Stopped LSB: disk temperature monitoring daemon. Dec 14 20:55:56 ab560 systemd[1]: nmbd.service: Succeeded. Dec 14 20:55:56 ab560 systemd[1]: Stopped Samba NMB Daemon. Dec 14 20:55:56 ab560 systemd[1]: Stopped target Network is Online. Dec 14 20:56:06 ab560 systemd-logind[532]: Failed to stop user service 'user@0.service', ignoring: Transport endpoint is not connected Dec 14 20:57:26 ab560 systemd[1]: tdm.service: State 'stop-sigterm' timed out. Killing. Dec 14 20:57:26 ab560 systemd[1]: tdm.service: Killing process 732 (tdm) with signal SIGKILL. Dec 14 20:57:26 ab560 systemd[1]: tdm.service: Killing process 1119 (tdm) with signal SIGKILL. Dec 14 20:57:26 ab560 systemd[1]: tdm.service: Killing process 1120 (tdm_greet) with signal SIGKILL. Dec 14 20:57:26 ab560 systemd[1]: tdm.service: Killing process 1138 (tdm_greet) with signal SIGKILL. Dec 14 20:57:26 ab560 systemd[1]: tdm.service: Main process exited, code=killed, status=9/KILL Dec 14 20:57:27 ab560 systemd[1]: tdm.service: Failed with result 'timeout'. Dec 14 20:57:27 ab560 systemd[1]: Stopped Trinity Display Manager. Dec 14 20:57:27 ab560 systemd[1]: tdm.service: Consumed 5.134s CPU time. Dec 14 20:57:27 ab560 systemd[1]: Stopping User Login Management... ... Dec 14 20:57:27 ab560 systemd[1]: Reached target Reboot. Dec 14 20:57:27 ab560 systemd[1]: Shutting down. Dec 14 20:57:27 ab560 systemd[1]: Using hardware watchdog 'iTCO_wdt', version 0, device /dev/watchdog Dec 14 20:57:27 ab560 systemd[1]: Set hardware watchdog to 10min. Dec 14 20:57:27 ab560 kernel: watchdog: watchdog0: watchdog did not stop! Dec 14 20:57:27 ab560 systemd-shutdown[1]: Syncing filesystems and block devices. Dec 14 20:57:27 ab560 systemd-shutdown[1]: Sending SIGTERM to remaining processes... Dec 14 20:57:27 ab560 systemd-journald[288]: Journal stopped