I think it can happen, especially because I often prefer smaller commits over bigger ones. But if the commit to be rebased was small understanding the conflict and resolving it is usually not hard. For me resolving conflicts has become mostely routine work, not the kind of horror it was when git reported the first conflicts to me in the beginning many years ago.

There is also a command git rerere that records how you resolved a conflict and lets you do it repeatedly the same way. A colleague has tried it and said it worked nicely (not sure whether it was exactly the case yiu describe). I suspect he spent many hours on learning it and I am not convinced it has paid off for him yet. I haven't had the feeling that I urgently want more automation. I just run my git diff --ours (and occasionally also --theirs) to make sure I don't make stupid mistakes during rebasing. And in the end of course git diff @{u}.