Make sure you model your stock in 360 so it knows there’s something there that it has to cut. There’s options for helical, ramps and straight plunges for your entry so you should be able to find something to work. Also where you select the tool there’s options for speed during these so you can slow down for the plunge if it’s been a bit nasty. If you are not breaking cutters you must not be too aggressive. Coolant, mist or air similar helps lots to keep it from sticking and helps clear the chips, recutting chips is bad.
Ya chips is a huge issue I really think I just have my stock size wrong