I created a rule where When Task is assigned, Do This Set assignee to rule triggerer and rule runs on Tasks and Sub-Tasks.
What I am trying to accomplish is automatically assign all sub-tasks to the parent task assignee however my rule isn’t working. Send help!! Thanks 
Recommend you share screenshots of both the rule, and and exploded List View of the Project where it’s not working as expected.
Note - I would also like the same behavior on a custom picklist from parent to child if possible 
OK, thanks for screenshots, that helps tremendously.
Given the caveat that I’m very new to Rules, I belueve the issue is that there is not a way in Rules to have the Rule applicable to a Parent Task also trigger action on the Parent’s Subtask.
A Rule can edit a Subtask, but only if the trigger is valid for the Subtask itself. Which in your case it can’t be…
I understand your use case, it’s quite logical and reasonable. I just don’t see a way to do it. Perhaps @lpb, @Phil_Seeman , @Richard_Sather , or @Andrea_Mayer can help, if I’ve missed something.
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I’m fairly certain this is not achievable using native rules in Asana.
However, I would strongly recommend to NOT assign all subtasks if they are to be completed by the assignee of the parent task. A very simple internal convention (best practice) could be put in place that: if a subtask is not assigned, it is understood that it is to be done by the parent task’s assignee.
Why? Simply because the parent task’s assign can use subtasks as a quick checklist, without having a bunch of subtasks (which may take a few minutes each) clogging up their My tasks. Instead, just the parent task is displayed in their My tasks, set with a start/end date, if necessary, to show the overall duration of the task, including all subtasks within it.
Your members will be much happier this way, if of course it works for your case and you don’t need to track subtasks in dashboards (i.e. how many subtasks each person has outstanding/overdue/completed etc). Consider it 
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