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Add range boundaries to the issue estimation. Use optimistic & pessimistic estimates to reflect alternatives and track how progress correlates to the estimated range.
Add a touch of real life for estimations by applying range estimates for issues you have concerns.
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Use JQL functions to look for issues you need to concentrate on. Filter issues that go beyond estimation range or run under the expected time.
Save efforts and time on checking the progress. Set a dashboard gadget to monitor issues at risk.