Hi, you can use the JIRA Suite Utilities plugin to set required fields for transitions - https://marketplace.atlassian.com/5048
If you need the red asterisks on the transition screens, you'll need to also use the Behaviour's Plugin - https://marketplace.atlassian.com/plugins/com.onresolve.jira.plugin.Behaviours
In JIRA Suite Utilities you can set workflow validator to require the fields you need. In the Behaviour's plugin you can create a behaviour for your project and get it to validate from the JIRA Suite Utilities.
You have two options, both done in the workflow.
A "condition" will prevent a transition even appearing unless the issue matches certain conditions. This might not be helpful as the transition will literally disappear completely, so your user won't know what to fill in.
A "validator" will check the entry of information on an issue as a user tries to transition, and reject it if it doesn't match.
Problem - there's no "field must be filled in" validator built into Jira, so you'll need to find or write a plugin to provide it. There are loads of these though - I use the one in the "Jira suite utilities" myself, but I highly recommend a look through the marketplace for other plugins that do it as you might find one that works better for you (the JSU one just demands that the user fills in one or many fields)
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