I usually try to cut (try is the operative word here) just enough to give a good sized opening but leave most of the shoulder of the head intact. Any more than that and I'm either spitting out tobacco or dealing with the rest of the cap, and eventually the cigar, unwrapping. A sharp blade is a must. Contrary to popular belief, cutters are not self sharpening, but the better ones last a longer time.
Edit: Be sure you hold the cigar as close to the cutter as you can to minimize movement and give it a good, fast clip.
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