Couple things.
How you hold your cutter can make that happen. If the cutter is cutting too aggressively it can be pulled out of the collet, chuck, or what ever you are using to hold it.
Could there be something going on that would be causing you to lose steps? I once had the opposite problem and realized that everytime I would go in for a cut the machine would bottom out and lose steps. Couldnt cut deep enough. Make sure your not hitting anything going up. Also make sure you are not trying to move too fast going up and lose steps.