Hi @Michael Arndt ,
This is a tricky one. Since the status of the issues is not changed when a sprint is assigned I don't think it is possible.
It is possible to require a field on an issue transition with a validator but since there is no transition when the sprint is assigned this is difficult.
You could edit your workflow so that when the sprint is assigned the status is changed and that transition would require an assigned user.
Thanks. I ended up adding a validator requirement to the transition to In Progress. That solved the issue.
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