Transmission Fluid Dip Stick.

There's a rubber stopper/seal under that cap beneath the handle, that's what is hitting on the edge of the tube. Jiggle it around so the dipstick is centered and it will push the rest of the way in.this stops about about an inch

There's a rubber stopper/seal under that cap beneath the handle, that's what is hitting on the edge of the tube. Jiggle it around so the dipstick is centered and it will push the rest of the way in.
This stops about 1" before it hits the top of the tube. Far before the rubber seal does.