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GUESS
He isn't crimping tight enough. Recoil shifts the bullets slightly forward in the case. Last round ==> saw six rounds worth of recoil to make this happen.
If the bullets he uses have a "fat" profile, and/or his barrel has a short leade/freebore, a bullet that's set a bit too far out in the case may engage the rifling before the slide if fully in battery. Apparently, the rifling grabbed the bullet hard enough that, when he knocked the slide back, it pulled the bullet free from the case and left it stuck in the barrel.
Several of the knowledgeable reloaders on the reloading area at M1911.org recommend testing any new round with what they call the "plunk" test: remove barrel from pistol -- hold barrel vertical, chamber up -- drop cartridge into chamber and listen for the distinctive "plunk" of the case hitting the shoulder -- turn over and verify that the round falls out freely.
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