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.
I have multiple projects that use variations of the same base workflow. The variations depend on the requirements of the project or issue type. The variations mostly come in the form of new statuses ...
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