You need to drill a pilot hole where you inserted the nail. The tip of the nail will break if you don't drill a pilot hole first. Unless you have a very weak mortar, I don't see how you can drive a nail into the mortar without a pilot hole. Everything I've read says you can just hammer it into brick or mortar and it will go in. I tried this, although my intuition was to drill a pilot hole first and the first tip of the nail broke after about 10 hammer hits. Save yourself the headache of drilling first, then hammering.
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