Either the configuration of the validator you have put on the transition is bad, or you've got an incompatible or buggy version of the JSU
First, check "manage add-ons" for the JSU version and check that it's valid for your version of JIRA.
Second, take a look at the validator config - they usual way to break one is to set up a simple check like "field xyz must be filled in" and then delete or make-unavailable field xyz. Sometimes, you get a polite message, but often a crash.
In the second case, or if it's neither of them, try removing the validator completely, and then re-adding it.
Ok, you have done everything right here, so I'm pretty sure you have found a bug in the JSU.
There's one last test I'd like you to do - split the validator. Set the existing one to validate on the user picker and then add a completely new validator (of the same type) to look at the date.
Does that work, or does it crash on one or both validators?
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