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The cutter should spin freely when it has bottomed out because there is nothing more for it to cut. If it is squeaking then it could be binding on the pocket walls. Basically you cut until there is no more resistance. Some pockets are already deep enough and you won;t have resistance at all. Others just need the corners trimmed out, and some need actual cutting of the pocket bottom to level out to proper depth.
As I posted above, do not press too hard while it is cutting brass or you will force the cutter to bite too deeply and it will spin the case between your fingers instead of cutting. Press gently while it cuts brass. When resistance disappears then I press firmly to make sure it is completely bottomed out against the case head.
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