The question is Would Jafar know to remove the Mask ? He has no prep or idea of who is up against.
I suppose not, but Jafar seemed like a relatively smart guy. Although he did fall for the genie bit...still, I don't know of any "weaknesses" Jafar had that Mask could use to beat him permanently. They could just wish/reality alter each other until Jafar notices the Mask is the only part of him that is not human looking (as he is often portayed as being human everywhere on his body except the face) so then decides to try and remove it from him.
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