Not directly - fields are made mandatory on an issue type basis, not assignee.
But you can add a validator to enforce it in the workflow. Two options:
- if you have access to one of the scripting add-ons, or can find an add-on which can do it, then the code for "if currentuser = assignee then check that field is filled before progression"
- If not, then you could have two transitions - one only for "assignee" and the other for "everyone else", and put a simple "field is filled" validator on the assignee transition
I think you can also do it with the Behaviours functions in the script-runner, but that could be bypassed by someone if they try.
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