The amount of rotations is key to sharpening. Usually when the tip is flattened, the DD has just started it's process. Always make as many rotations until the grinding comes to a stop. The way the machine works is it will remove the chisel, put a new one on and then remove the rest of the material in a spiral motion down the face of the bit. The last spot it will remove material from is the heel.
The alignment & depth wasn't set properly
Make sure when setting the depth of the bit that the drill has enough stick out. The best way to ensure this is to hold the bit against the wheel when tightening it in the chuck. This will also prevent the drill from "backing" out. As for the alignment, the guides need to be resting inside the flutes.
The drill that is being sharpened is originally 135 degrees.
A 135 has more pitch to it. It's a lot flatter and has a longer chisel. A 118 has a more aggressive tip with a smaller chisel. The DD350X cannot recreate the 135 so more material removal is required to get a properly sharpened bit from this machine. The user may have to repeat the steps once or twice.