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When the status changes, I want to copy the value of a user field to the assignee field. This works if the user field is single select. However, it doesn't work if its multi select. Anyone else seen this before? Is there a work around?
That's correct, the assignee field is single user, trying to copy a multi-select into it is nonsense, the data structure isn't supported.
You'll need to use single-user fields, or do a bit of coding to decide upon and extract the account you want to assign the issue to from the multi-select data.
If you are on Jira Cloud using the built in Automation for Jira (which I'm guessing you are?) then this might be helpful.