I have a pair of 110 actions that I made into 308win and 22-250. The 270 blind mags(both started as 270) would feed the 308 perfect, but the 22-250 would do as you have drawn. I came to the conclusion that the bullet tip needs to be in the chamber mouth before the case head comes out of the magazine lips. I am not sure of the solution for yours, but I ended up buying a short action magazine and making an adapter bracket to mount it into my long action.

Hope that helps,
Adam.

Edit.
What was happening on mine, and I believe yours, is that the bullet tip is not in the barrel, but against the rear of the barrel.