Work requests that are in error (and not failure) cannot be restarted
If you look at https://debusine.debian.net/debian/developers/work-request/149099/, you will see that the work request ended up with an error due to an intermittent network failure. And it can't be restarted (neither in the UI — there's no button for it, nor in the client — it fails with "Only aborted or failed tasks can be retried").
Given the error message, this seems to be a design decision but I'm not sure that it was a good choice. Arguably some error (like validation errors) will happen again on a retry, but other errors might not.