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@Coby Fuller you could also add into the automation suggested by @Darshan Mandhane an email (back to the initiator) or a slack or Teams message to a channel letting them know the date had changed and to add a comment providing a relevant justification for the change....if you like?
Reactive rather than proactive I realise, but easy to do.
I am adding a screenshot of what I meant.
You may also write variable substitutions in the comment if you want to put the actually changed date timestamp.
Official documentation on same: https://www.atlassian.com/software/jira/guides/expand-jira/automation
@Darshan Mandhane Thank you for taking the time to respond. I had considered this and even had the rule created, but decided to remove the automation rule. I would like to for the teammates to get into the habit of adding a comment if they need to change a date. Automating a comment that they typically ignore just was not working.
Depending on the number of statuses in your workflow, this could be a lot of work... but perhaps put the Date field on only the View screen(s), so it cannot be edited. Then add a loop transition (transition to and from the same status) to all relevant workflow statuses called Change Date (or something to that effect). Create a transition screen for this loop transition and add the date field. Add validation that a comment must be added - the validation message can state "Provide a reason for changing the date in the comment field."
That's the only way I can think of enforcing a comment for a date change out of the box.
@Greg Williams (ZTR) Thank you for taking the time to respond. Although this does make sense to me, the workflow that I would need to add this to is a monster. As you stated above, it would 'be a lot of work'. From my perspective, this is all about communication and the team needs to get better at it, and get into the habit of adding comments if they change date fields.
Not OOTB. If you were using CMP then you can require a comment using a validator on the workflow transition. However if you’re just updating a field then you would have to construct a listener that would watch the date field and then present a modal for the comment. This would require an add-on such as scriptrunner or similar.
Automation is more for "backend" algorithmic responses to changes in Jira (not "front-end" / GUI). There is no support for interacting with a user, beyond manually triggering a rule to execute.
Workflow interaction is limited to status changes (transitions), where a screen can be involved to offer optional fields and enforce required fields in order to complete a transition.