Shoulder bump problem or no problem?

This is what I think as well.
Your case web area is the tight spot and running the die down a couple of times to bump the shoulder back more eventually gets the web down to fit.
It may not need .008 shoulder bump.
It may be the case web size.

I'd first do what 26Reload said and run a scope and/or polish the chamber for possible burrs or ridges if needed.

FYI... It has happened to me in a 284 Win chamber. I ended up switching brass and the web problem went away.

Just my thought!
I agree that this is what's happening, but I think a burr needs to be removed. It's a Sherman Mega. Not really a parent cartridge to it, but is basically an elongated WSM. ADG brass
 
Sounds like case web. Before my custom dies on lapua case id run it through a 33xc die first to size case web then id bump it in a redding lapua ai die to get me by. This is just reference for what's probably going on… also causes clickers
Yup... I had clickers in that 284 Win while when I had the same problem.
 
IMG_4046.jpeg
This is a pic of the mark at the web. It's really small but obviously making contact.
 
The pic I sent shows a small mark. Very small. Just in that one spot. It's hard to tell by the pic but 1 spot on that mark is very shiny. Almost looks like the brass got dug into.
 

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