Systemd custom target stops working after migrating from version 252 to 255

Recently we upgraded our systems from Flatcar stable 3815.2.5 to Flatcar 3975.2.0. This means we moved from systemd version 252 to 255.

Our systems are configured with a custom default target called online.target.

ls -l /etc/systemd/system/default.target
lrwxrwxrwx. 1 root root 33 Aug 16 09:41 /etc/systemd/system/default.target -> /etc/systemd/system/online.target

Two services depend on this target by means of a WantedBy=online.target in their respective service files. One is a Type=oneshot service which runs a custom activation-check.sh script, the other is a Type=exec service which runs the Bird routing daemon.

In addition, there is a directory /etc/systemd/system/online.target.wants which contains symlinks to the services mentioned earlier.

The problem is that the system says it has succesfully reached online.target, but the activation-check.service was never started.

Logging says:

Aug 16 09:44:09 dev-ns01 systemd[1]: Reached target multi-user.target - Multi-User System.
Aug 16 09:44:09 dev-ns01 systemd[1]: Reached target online.target

However, when I manually change to the online target using systemctl isolate online.target everything works perfectly fine. So that tells me the dependencies are configured correctly, right?

I have looked through the changelog from systemd 252 to 255 but have found nothing related to this issue. Anybody have a clue?