Take a very close look, under good lighting, at the fired cartridge case (a cartridge is the unfired assemblage of cartridge case, primer, powder, and bullet). Can you see any irregularities on the surface, heavy scratches, bumps, annular ridges or depressions? The chamber of your rifle may be corroded, pitted, "ringed" - that is an annular depression in the metal, or some other problem.

How does the primer look? Is it very flat, and completely (or nearly so) fill the primer pocket to the edge with no rounded primer edge - a flat that continues from the primer surface to the case head without a depression at the edge of the primer?

You may need to take the rifle to a gunsmith to be diagnosed, or to a knowledgeable friend with lots of experience with shooting old rifles.

Can you post a picture taken close-up with your camera on macro setting, and with good lighting on this forum? Actually, two photos, one of the side of the case, and one of the head/primer.

Trigger Happy wrote on Apr 3^rd, 2017 at 11:18pm:


What model rifle is it? A model 1885? 1894?  I'm assuming it's a model 1885 High Wall. You might try google "image" - i.e. google "Winchester Model 1885" rifle parts diagram".

Cleaned before and after shooting. Inspected case, seems ok. Another shooter gave me a sized 38-55 case. Inserted in chamber, worked the action. Stuck. I won't shoot it until the club starts regular Wednesday shoot days. But on a weekend with nice weather and a new (old) gun staring at you, I had to do it.

Ends

How hard do they insert to start with? Have you mic'ed the fired cases to see if there are wide spots or major deviations to the unfired cases? Primers kind of look backed out in photo or is that just optical delusion

Thanks for posting the pictures of the cases. I don't see anything in the picture that shows a rung chamber or heavy pitting.

Still, the culprit seems to me to be either a rough chamber or a tight chamber at the base.  Look at the fired cartridge case again, but in subdued ambient light, and shine a flashlight at a low angle or parallel to the side of the case to highlight any abnormalities with the case.

The High Wall does have a bit of camming to push a reluctant cartridge in the chamber the last little bit. With the chamber open, but the lever pulled back just a bit to let the extractor go fully forward, can you seat a sized case fully with just your fingers, or does it balk at going in the last bit.

Do you have a 30-30 sized case that you can try chambering by hand? With it's greater body taper, if you do get resistance, you know that it's coming from the bottom part of the case.

With the possibility of a pitted chamber, I'm reluctant to do a cerrosafe chamber cast, as pitting can grab the side of the cast and make it difficult to remove from the chamber.

I just read Quarter_bore's post - good points.  Can you remove the forearm and see if there's an extra dovetail for the mainspring base? If the barrel was set back, they would have had to cut a new dovetail for the mainspring base.

I looked at the photos and see only the one primer that's flowed into the pin hole- not horribly, but....pressure isn't likely high, but you may have some wear on the block's hole.
Nobody has yet asked if a new, unfired load will chamber by finger pressure and extract. If it will, something is happening upon firing, and then all this other advice will be more meaningful. 
Don't bother to stick a .30-30 in there and expect to learn anything. That case has a different shape ahead of the base that will stop in no time. Hope you get 'er going soon and glad to have ya here.