I reviewed the question: Destination status could not be resolved. If using a smart-value ensure this resolves to a numeric s, but I don't think it applies to my case. I am getting the error:
Destination status could not be resolved. If using a smart-value ensure this resolves to a numeric status ID or untranslated name for issues (with current status): DOPI-727 (In Progress - 3)
The rule I have is preventing transition an issue to IN PROGRESS if the issue is unassigned, so it transitions it back to the previous status. The problem I am getting is that sometimes it works and sometimes it doesn't for the same issue. Here is my rule, it seems to be large, but the logic is simple, just we need to consider different scenarios an message based on the issue type:

I highlighted the portion for the subtask. As you can see from the Automation log. Note: I added the edit condition for start date after the log execution, so you don't see this edit condition in the log. Subtasks haves standard workflow TODO<->IN PROGRESS< ->DONE. Allowing backward transition from current status to the previous one:

The first time the condition is triggered the rule successfully executed, when the user transitioned an unassigned issue from TODO to IN PROGRESS:

but the second time (about 15 mins after the previous trigger) failed. The rule was triggered when the user did the same operation. I got the error message:

Here is the issue history:

I highlighted when rule was triggered.
In this case, the workflow is the same, so I don't think there is workflow post-condition or function. The rule works because the first time for the same issue it worked, but for some reason it fails the second time and according to the issue history, nothing specific happened.
I am trying to find any specifics for the second case that justifies the fail, but I am not able to find it.
Any help is appreciated,
Thank,
David