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Based on the add-on documentation, the checkbox triggers a transition if the transition is named in a certain way and is available based on the current status.
What would be even better if the add-on would determine the transition to be triggered on a checkbox based on the target status (to be configurable). For example, if the target status is "Done", it should be known which transition should be invoked based on the current status.
Also, if there are more than one transition leading to the target status, the choice should be shown (or the priority of transitions should be configurable).