Hello again.
If the nut doesn't form a complete seal the transmission would be more prone to leaking due to high transmission pressures. So, to answer your question yes, it will leak if not sealed correctly. The fill level/plug will have a rubber o-ring to help seal the transmission and plug/dipstick from leaking. I've attached pictures below. Hope this helps and thanks again for using 2CarPros.
Danny-
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Monday, April 20th, 2020 AT 3:53 PM