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Why was a work item not reassigned to the coverer?

Check three things in order: the coverer can be assigned work items in that space, the coverer is not out of office themselves without a coverer of their own (the app follows such a chain for up to 5 steps), and no Jira automation rule is assigning the work item back.

The rule's Reassignment Log lists every work item it could not move, with the error each hit.