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In our workflow, if an issue is not passed in Testing, we can move it back to In Development. However, it does not always move back to In Development because it fails testing. But, it could move back because the spec changed.
So, is there a way I can have two transitions in this workflow back to In Development, which would allow the tester to choose a reason the issue was moved back?
How do you want to document the reason for the transition?
Are you going to provide a custom field where the user can type in the reason, or select from a list of reasons?
If so, then you can use just one transition, and include a Screen on that Transition where that screen includes your Reason field and have the user select the reason.
Including a Screen on a Transition is available only for workflows used in Company Managed projects.
Are you a Jira Administrator? Only a Jira Admin can make that sort of change - creating a new custom field, creating a screen, and modifying a workflow to attach the screen to a transition.
This page includes information about using a screen with a transition.
Yes, you can have 2 different transitions from 1 status to another. Each transition can then have its own transition screen with other fields if needed.