Make Precision Drilling Easy with AutoAngle Drill Guide! The World’s Most Accurate Angle Drilling Jig is On Sale, But Only for a Limited Time! There are several challenges when drilling angled holes. First is getting the angle correct, next is getting the direction of angle correct, and perhaps most important, you have to get the entry point correct. It’s tough enough doing it on a drill press, but when you have to do it in the field or on a large workpiece, the challenges get…more challenging.