Yes that's possible. To do exactly what you describe, you will need a few things. I recently answered a very similar question about entering a comment on a transition. You can find the description here: https://answers.atlassian.com/questions/42693071.
That's actually it. You can go one step further and add a validator to your transition to make the field required.
And that should do the trick.
Hello Atlassian Community! My name is Emilee, and I’m a Product Marketing Manager for the Marketplace team. Starting with this post, I'm kicking off a monthly series of Spotlights to highlight Ma...
Connect with like-minded Atlassian users at free events near you!Find a group
Connect with like-minded Atlassian users at free events near you!
Unfortunately there are no AUG chapters near you at the moment.Start an AUG
We're bringing product updates and pro tips on teamwork to ten cities around the world.Save your spot