Gabel, I have also seen the same thing. The bit wasn't long enough so the builder hacked at the exit side to expose to peg hole, the funny thing is he didn't expose the hole and gave up. In the repair of this tie beam to rafter connection, I finished boring and he was only an inch away. The tie was wider at one end than the other to save on a lot of hewing, they were like this through the whole building, flared ties.

It helps to keep your joinery closer to one side due to the chance that the deeper the peg hole is from the starting face the higher the chance of wandering of the bit and that could lead to a pushed apart or too tight joint. I also drive all pegs from the ref. face. Are you using a guide for the peg holes, or just a square. Tim