Howdy
The Model 1892 Winchester and its replicas uses a tilting carrier to raise cartridges up from the magazine and feed them into the chamber. Not much different than the ramp in a 1911 pistol that cartridges ride up to feed into the chamber. And just like the 1911, sometimes a cartridge will have trouble entering the chamber if a sharp corner catches on the edge of the chamber. This is not a problem with the toggle link rifles, such as the 1860 Henry, 1866 Winchester, 1873 Winchester and their replicas. These rifles feed cartridges straight out of the cartridge lifter into the chamber, much like torpedoes being loaded into torpedo tubes in a submarine.
When I was loading 38 Specials for Mrs Johnson in CAS I always loaded her 38 Special rounds with 125 grain truncated cone bullets, on the left in this photo. Round Nosed Flat Point bullets will also feed very smoothly. A Semi-Wadcutter bullet, like the one on the right in this photo, may or may not feed smoothly in a '92. The sharp corner may or may not catch on the top edge of the chamber. It depends on the individual rifle.