Rubber gasket "tight fit" simulation

Hello all,

I am trying to find out how much force I need to apply to a part in order to deform a rubber gasket enough to get it to pass through a constricted area. I have set up a non-linear dynamic simulation with the gasket and the outer and inner metal profiles. To make processing time faster, I only have a 1 degree revolve of each of the parts. The lowest part is fixed completely. The upper metal part has a cylindrical fixture (no movement) and a fixed downward displacement of 30 mm.

I want to squeeze that gasket and see how much force it takes on the upper metal part to get it through. It should be easy enough but I get an error every time.

Does anyone have any ideas? I've included the files in this post. Thanks!

Context: This gasket is what's called a "shear gasket". Notice that it has a hook shape. It is meant to pass through a tight spot (like the one modeled above) in order to hook onto the metal profile below. The purpose of this is to provide some resistance being pulled back up involuntarily but at the same time allow it to shear (and those allow part recovery) when pulled on with enough traction. Basically you push the part down and can only pull it back up once you have enough tension to shear the gasket.

SolidworksSimulation