The original Winchester 92's were designed to work with bottleneck ammo in the 1.5" to 1.6" OAL with round nose flat point bullets. Ammo like 44-40, 38-40, 32-20 and 25-20.
What that means is they may not work well with really long 357’s or really short 38’s.. The really long 357’s are too long to clear the cart stop coming up or they tend to hit the top inside of the chamber before they make the turn into the chamber.
The most common problem with the shorter 38's is the gun will throw out, flip or stovepipe live rounds with the empty's. This is because the shorter 38 coming on to the carrier from the tube can bounce forward enough that the rim is too close to the rim slots in the guides and when you lever it fast the carrier just catapults them up or out with the empty. (One of the things Rossi did years ago was redesign the cart guides by changing the angle of the rim slots so the back end comes up sooner. So they tend to be less ammo sensitive than other pistol cal 92 leverguns)
Also, bullet shapes can make a difference. Bullets other than the round nosed flat point profile they were designed for can cause issues. The truncated cone or TC style bullets will work but can end up too long for some guns.
For 38’s, this is what I have found to cycle best. A 158gr elongated round nose flat point seated above the crimp groove and just crimped into the side of the bullet just above the lube groove. This allows them to be loaded to a 1.5” OAL. You can do the same with the 44 spec. too.
For years there were commercial reloaders that offered CAS ammo, offered 1 1/5" long loaded Cowboy leveraction 38's.
I directed my rifle customer to "T" ammo for his 1.5" cowboy 38's. But, Roy retired so I was recommending Ammo Direct.
Well, they are out of business now. (had a fire I believe)
Here is the new source.
CUSTOM AMMO & RELOADING SERVICES,LLC
3110 Marble Court
Granbury, Tx 76049.
they sell this ammo and will also reload your brass.