I noticed the case gouge in that pic. It's why I wanted to see pics from different angles. That pic may hold the key.
277 rounds total at this point. 50 rangers, the rest 230 gr WWB. Roughly 150 rounds total before I ran the rangers, though. No FTE in that time, and only one FTF caused by me not fully seating the magazine.
Just from looking at the torn off case rim I'd say your extractor is toast. (if it wasn't before - it is now) Number your mags and if one is the trouble maker measure the feed lips with calipers. If the bad one is wider than the other mags - toss it. It looks like you had a hard push feed or inertial feed with the extractor behind the rim and then dragged the case through the lips. What recoil spring weight are you running?
If WWB runs fine in your gun, I'd just keep shooting that. For now use it as your SD ammo (it's still .45.) After you get a flawless few more hundred rounds down the tube, you can revisit the hollow points again. Your gun is still new and settling in.
It is a new to him gun. Doubt it has been changed from stock offering.
If fixing my grip doesn't resolve it and it's not isolated to 1 or 2 magazines, I'll see if I can get my hands on some of other manufacture to try out.It's definitely a Springfield. I know that by the vertical indentation in the case in your picture. It's usually not an issue though.
I'd try a different mag like a Wilson, EB, CMC before I did anything else. The damage I see in the empty casing is from jamming between the slide and frame and is to be expected. It's from the rear forward.
One thing I never rule out is any Winchester AMMO quality control. I've got 1952 and 1956 surplus ammo that's better than any Winchester I've gotten in the last 6 or 7 years.
IF it says Winchester on it, newer than 6 years old, it's junk. I won't use it. The only fails I've had have been with Winchester and some HPs in cheaper guns