There are many things which can cause damage to the cartridge cases. Yes the timing of the ejection in relation to the load used can cause some issues.
If the barrel unlocks from battery too soon and the brass still has enough pressure to expand and hold it to the chamber walls the extractor can do some damage. (more of a problem in semiauto rifles)
Sometimes they get damaged just by being smacked around by the returning slide either during feed or ejection. The breech face if not smooth enough or dirty could hamper the feeding process as the cartridge rides up the breech to be pushed into battery. Sometimes in the situation of stovepiping(brass trapped by the returning slide) will dent or bend things. They can also sustain damage by hitting the pavement or hard surface while the brass is hot from being fired.
I find some extractor rims (bent, dinged up) which will not enter a shell holder for reloading so These should be removed and not used, this can cause a failure to feed problem. Not a good thing!
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