I'll simplify my requirement so it may not make complete sense as to why I want to do this.
I have a custom multi line text field. I would like to populate this with the current user when a certain transition happens in my custom workflow. Is this possible?
Strictly, no, because the current user is a user object, not a block of text. The best you could do is convert the user object to a string representation in a post-function and drop that into the text. But it will no longer be a user, just some information about that user in plain text.
You will need some code too - I'd write a script-runner post-function to do it, but it would be quite short, as extracting a user name and/or login is quite simple
Neither. As Zezeto has said, you use a scripting add-on. I use the script-runner because it's been the most powerful one for many years (with the caveat that with great power, comes great responsibility - you must understand JIRA before you try to write your own scripts) and I've got used to it. Also, I now work with Jamie, so when I get stuck, I can directly ask his team for help, but I'd have said the same thing even if I didn't.
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