I would like to force my users to put a comment on a bug issue when they are closing it or setting the resolution to a specific state such as "cannot reproduce" or "won't fix"
Today, comment is not mandatory so we are missing some information.
you can write a workflow validator as
InvalidInputException e=new InvalidInputException();
e.addError("comments","Comment must be filled");
if incase resolve:
I presume the required comment is for tracking purposes. Rather than doing that, I suggest creating a custom text field named something like 'bug close comment' and making it mandatory at the close transition. That will allow you to easily seach for similar comments for all bugs at time of closing.
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