The extractor was way loose. Only thing I could figure was it was loose enough that the ejector just pushed the case instead of there being a "springing" action ejecting the round because of the extractor tension, so the round just got pushed aside a bit, but stayed in the extractor, then the next round in the magazine pushed the spent case back against the bolt face as the new round was being fed into the chamber.
Pretty f-ed up, never an extraction or feeding problem from the magazine. New extractor, properly tuned, fixed the problem.