No reason why a case which extracted easily could be too big to fit in again. The brass always springs back to a smaller size after firing. So what came out, must go back again. And without a struggle...

Hmm.... sometimes it is difficult to close a bolt over an empty case because the extractor claw has to click over the rim in the almost-closed-bolt position.
If so, one solution is to put the cases in the magazine so the extractor claw slips naturally over the rim as it feeds up out of the mag. You may need to steer the case mouth into the chamber with your finger because the bullet is missing. Or you may need to do the fitting of the extractor claw over the rime by hand. Main thing is that the claw should be over the rim before you close the bolt.
Try it and see?