We have run into this numerous times on our old Haas's. If the back feed is set at anything faster then about 200IPM they will clip a corner of the part on back feed. what machine are you running the parts on?
Use the roughing option with circlemill to spiral out. works awesome. if you uncheck the helix entry the endmill will plunge into the hole then spiral out, can also add a finish path in the same toolpath.