Hi Tomer,
Yes, this is a great fit for Jira Automation. Here's the general pattern:
1. Set up a scheduled rule (Trigger = Scheduled, run it once daily)
2. Add a JQL condition to catch issues where the assignee's had it open for exactly your target duration, something like: assignee is not EMPTY AND status = "In Progress" AND created <= -14d AND created > -15d — that narrow range is what keeps it firing once on the right day instead of every day after the threshold
3. Action: Send email (or Send notification) to the assignee asking them to update the status
I've built something similar before for a recurring compliance check-in, and that exact-day JQL range is really the key part — without it you'd end up emailing people every single day past the 14-day mark instead of just once.
If you want it to repeat every couple weeks instead of a one-time nudge, just adjust the JQL to check for multiples of 14 days instead of a single window.
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