Is it doable?
I've asked if possible to modify Jira issue status based on comparison of two fields:
If possible, we would like the JIRA to automatically mark the status as Closed when all the “Verified Versions” are equal to the “Fix Versions”.Also, if possible, to block marking status as “Closed” in case the “Verified Versions” are NOT equal to the “Fix Versions”.
Don't know about triggering a transition if 2 fields meet certain criteria but for the other idea (blocking the transition unless those fields meet the desired criteria) I'm thinking you could install the free plugins Workflow Enhancer and JIRA Misc Custom Fields. From there just create a custom field "X" that compares your 2 fields and setup a condition in the desired transition within your workflow so it can only be executed if the value of "X" is whatever you have chosen.
I hope this was somehow useful and I wish you the best of luck finding a solution for the automatic transition.
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