I'm trying to add the "Log Work" to the "Assign" screen that pops up when I click the Assign Button when viewing an issue from my Board.
Welcome to the community. The only option I can think of is the following, however I am not aware it is possible to trigger the Log Work screen when you assign the issue via the Issue View screen.
Here is my option -
1) Remove "Assignee" field from your EDIT ISSUE screen.
2) Move the issue assigning operation to be a part of your WF transition process.
3) In the appropriate WF transition, set validator to make Assignee field to required + Time Spent field to required. Also associate the transition with a WF transition only pop-up screen by adding the Assignee and Time Spent fields to the pop-up window. So when an issue is transitioned, one will have to assign the issue and provide the time spent (log work) to complete the transition. Example - customize the transition from OPEN to IN PROGRESS.
The drawback of this implementation is that the issue assigning process can only be done via WF transition.
Hope this may helps.
Best, Joseph Chung Yin
Jira/JSM Functional Lead, Global Infrastructure Applications Team
Viasat Inc.
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