Thank you for taking the time report a bug and make Ubuntu better.

I haven't tried to reproduce the problem, but I have a few
considerations here.

After a quick search to check whether this problem was already
encountered/handled by other distributions, I found an interesting bug
against chrony on RHEL 8 which has the following comment:

https://bugzilla.redhat.com/show_bug.cgi?id=2015335#c3

I'll paste the interesting part here:

"The default chronyd service cannot be restarted automatically on
failure, because that would break the expectation that the clock can be
stepped only on boot or intended service restart. The default
chrony.conf has "makestep 1.0 3", which allows the clock to be stepped
only in the first three updates of the clock. Allowing steps at later
updates might have security implications."

This is valuable insight that certainly has to be taken into account.

As such, my reaction is to mark this bug as a Wishlist for now and
recommend a few things:

1) If the considerations pasted above are not concerning in your
scenario, my advice is to modify the original systemd unit file (via
"systemctl edit" or drop-in files under
/etc/systemd/system/chrony.service.d/) and adjust it according to what
you described.

2) It would be great to start a broader discussion about this topic with
the Debian maintainer, because they may have more insights about the
package.  If you can, feel free to file a bug against the Debian chrony
package and then paste its link back here so we can track things.

Meanwhile, I believe we should refrain from making these modifications
to the original package due to the security concerns raised above.

Thanks.

** Bug watch added: Red Hat Bugzilla #2015335
   https://bugzilla.redhat.com/show_bug.cgi?id=2015335

** Changed in: chrony (Ubuntu)
   Importance: Undecided => Wishlist

** Changed in: chrony (Ubuntu)
       Status: New => Triaged

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https://bugs.launchpad.net/bugs/2089576

Title:
  Chrony systemd service isn't restarted in case of an error

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