Gas check dislodging concern

[357Maximum]

Question about a concern. I have some .360 sized GC LBT bullets for shooting in my .357max.
I crimp these in a Lee crimp die. It is somewhat difficult to ram the cartridge into the die because of the .360 bullet diameter. I have to exert quite a bit of force in order to get the bullet into the die. My concern is; Is it possible that the gas check could be forced off of the bullet inside the case due to the excessive pressure required to penetrate the die?
I believe this die must have an ID of around .362” at the collar which is pinching the case in effect resizing the cartridge.

What are your thoughts on this theory / concern?