I found these two bug tickets that could be relevant:

https://github.com/home-assistant/operating-system/issues/896

https://github.com/systemd/systemd/issues/8683

I should also add that this seems to happen on the majority of boots for
me, but not every boot. So there is some amount of non-determinism
involved.

I'm not familiar with what service / tool / part of kernel does what in
the boot of an Ubuntu 20.04 system, but I might read up on what systemd-
time-wait-sync.service waits for to see if I can figure out why that
does not happen.

Anyway, thanks for helping me debug this issue!

** Bug watch added: github.com/home-assistant/operating-system/issues #896
   https://github.com/home-assistant/operating-system/issues/896

** Bug watch added: github.com/systemd/systemd/issues #8683
   https://github.com/systemd/systemd/issues/8683

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https://bugs.launchpad.net/bugs/1937238

Title:
  systemd-time-wait-sync.service stuck in "activating" state after boot,
  blocks timers from starting

Status in systemd package in Ubuntu:
  Incomplete

Bug description:
  When I start my server running Ubuntu 20.04 the systemd-time-wait-
  sync.service is stuck in "activating" state. I noticed this because
  none of the systemd timer units triggered, because all the timers
  depend on systemd-time-wait-sync.service. Running "systemctl restart
  systemd-time-wait-sync.service" manually works around the problem.

  Some logs and command outputs:

  raek@mizar:~$ lsb_release -rd
  Description:    Ubuntu 20.04.2 LTS
  Release:        20.04

  raek@mizar:~$ systemctl | grep systemd-time-wait-sync.service
    systemd-time-wait-sync.service                                              
                 loaded activating start     start Wait Until Kernel Time 
Synchronized

  raek@mizar:~$ systemctl status systemd-time-wait-sync.service
  ● systemd-time-wait-sync.service - Wait Until Kernel Time Synchronized
       Loaded: loaded (/lib/systemd/system/systemd-time-wait-sync.service; 
enabled; vendor preset: enabled)
       Active: activating (start) since Thu 2021-07-22 11:06:52 CEST; 27min ago
         Docs: man:systemd-time-wait-sync.service(8)
     Main PID: 514 (systemd-time-wa)
        Tasks: 1 (limit: 9415)
       Memory: 972.0K
       CGroup: /system.slice/systemd-time-wait-sync.service
               └─514 /lib/systemd/systemd-time-wait-sync

  Jul 22 11:06:52 mizar systemd-time-wait-sync[514]: adjtime state 5 status 40 
time Thu 2021-07-22 09:06:52.216338 UTC
  Warning: journal has been rotated since unit was started, output may be 
incomplete.

  raek@mizar:~$ journalctl -b -u systemd-time-wait-sync.service
  -- Logs begin at Wed 2020-07-08 16:34:13 CEST, end at Thu 2021-07-22 11:36:44 
CEST. --
  Jul 22 11:06:52 mizar systemd-time-wait-sync[514]: adjtime state 5 status 40 
time Thu 2021-07-22 09:06:52.216338 UTC

  raek@mizar:~$ dpkg -S /lib/systemd/system/systemd-time-wait-sync.service
  systemd: /lib/systemd/system/systemd-time-wait-sync.service

  raek@mizar:~$ apt-cache policy systemd
  systemd:
    Installed: 245.4-4ubuntu3.11
    Candidate: 245.4-4ubuntu3.11
    Version table:
   *** 245.4-4ubuntu3.11 500
          500 http://se.archive.ubuntu.com/ubuntu focal-security/main amd64 
Packages
          100 /var/lib/dpkg/status
       245.4-4ubuntu3.10 500
          500 http://se.archive.ubuntu.com/ubuntu focal-updates/main amd64 
Packages
       245.4-4ubuntu3.8 400
          400 http://archive.ubuntu.com/ubuntu focal-proposed/main amd64 
Packages
       245.4-4ubuntu3 500
          500 http://se.archive.ubuntu.com/ubuntu focal/main amd64 Packages

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