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Hi @Jason Liu
@Fabio Racobaldo _Herzum_ is correct - Jira's built-in capabilities do not allow for customization of the log work dialog, but that does not mean it's impossible.
If you're fine with using a third-party app, I gladly recommend our Clockwork Free. It asks for a worklog description by default, and you can configure the dialog to make adding the description mandatory.
Clockwork is well-known for its automated time-tracking mode, but please note that the feature to make description mandatory only works when a user manually adds a worklog or stops a running timer. Automatic timers do not show the log work dialog when they are stopped, so the users are not asked to fill in the description.
With Clockwork Pro you can further customize your log work dialog by adding custom worklog attributes.
Let me know if you have any questions.
Oops, my bad, sorry. Clockwork is Cloud only.
In this case, I'd look to ScriptRunner - maybe you have it installed already, it's extremely popular.
I have no experience with that tool, but maybe there is someone else here that can help with that.
Best of luck!