Steps on How to Improve This Feature

1. Ensure that you have the Misc Workflow Extensions plugin installed in your instance.

2. Edit the workflow associated with the reported project.
3. Add a new post function called Transition parent issue to the Start Progress transition.
4. Add the ID of the Start Progress transition to the Transition: field:
   
   
5. Ensure the Post-Function is displayed on the transition per the example below:
   
   
   
6. Apply steps 3 and 4 to the following transitions to make the whole thing seamlessly:
   
   1. 進行停止 
   2. reopen
   3. Reopen and start progress
7. Publish the newly enhanced workflow.
    More information on how to add post functions can be read from here.
    Documentation for the Transition parent issue post function can be read from here.

Testing the Feature

Now, attempt to transition issues from one column to the another column in Work Mode. As long as you're transitioning a sub-task from a list of sub-tasks, you will notice that the parent issue's status will follow the moved sub-task's status: