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I created a select list (custom field) in issue. if it is not selected and "To do" status is changed to "in progress" or "in review" or "Done" a pop up should show.
(Without selecting field values status should not changed)
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Jira does a pop-up automatically if you add a "transition screen" to the workflows.
However, it is not conditional, you can't choose not to show it.
There is a trick to this though - create two transitions to the same place, one with a "condition" that says "only if field is empty" and the other with "only if field is filled"
You'll need to do a pair of transitions for each status you want to go into.
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