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case shoulder dents

I was doing case prep on some Remington 280. I had a stuck case this weekend and had problems getting the case out. Today after removing the primers, I noticed that the shoulders of most cases had dents in them. What could have caused this problem ? Thanks for the help.
Comments
Most loading books will have pic's and lengthy detailed written description of case lubing.
One small can, a little dab on the fingers, rub the case and go, will do many many cases.
Don't mess with sprays, lube pads, etc. Hit the "easy button".
Everyone has a favorite lube. They all work. Personally I find Imperial is overhyped and overpriced. Works great, don't get me wrong, but it's slow to use and doesn't work any better than the Lee paste stuff that's a third the price.
Of late I've just been drizzling a little motor oil on my lube pad and using that. Works great. It is, after all, designed to prevent friction between two moving metal surfaces. Naturally you have to remove it all after sizing, or the oil could contaminate the case; but I could say the same about most lubes on the market that cost a lot more.
Correct: The lube also contaminates the polishing media very rapidly.
I bought a Lyman ultrasonic cleaner few years back and it is great for removing the lube before sending to the media. It's also very good for cleaning small engine carb's.