I'm thinking more along the line that when the bolt is locked back with the charging handle, the spring that pushes the bolt release down also pushes the magazine out of the magwell via that little tab on the back of the magazine. This is the, "hey, it pops out freely" mode. So, not only gravity pulling, but spring pressure is pushing the magazine out of the well.
When the bolt is locked back by the bolt hold open/bolt release, that little spring on the bolt release is out of the picture, making gravity the only force acting on the magazine, which may or may not stick.
Remove your trigger group/magwell out of the gun and bench test it. With magazine inserted, hit the release and watch the bolt catch drop with the magazine. Then, hold the bolt catch up (as though it is engaged with the bolt) and hit the magazine release. You may find that it sticks just like it does in the gun.
I did some light sanding on the front flat part of one of my 20s and it seems to fall a little easier than before. I think the light weight of the 20s and a little bit of friction keeps them from falling freely. If you do the mag flick maneuver, they come right out. I wonder if adding a little weight to the base plate would help...