First, to solve your problem it would be great for us to have an example file.
Second, I see you've got an expression 'Status'.
Is this Status(=Closed) your expression or is Status a field name?
If it's a field name, you should consider renaming your label for the expression "Status".
You know, when you spend so much time trying to do something and you get stuck over and over again trying to solve it.... you pass things like that.
I just changed the Expression label and the condition started being evaluated flawlessly.
I needed a fresh pair of eyes to see this.
Thanks for the quick response Fred.