How To Loosen A Stuck Drill Chuck. If the chuck is not releasing the bit and it is really tight try using WD40 to loosen it and extract the drill bit. Answer 1 of 7.

BUT when in use the keyless chuck comes loose and the drill bit does not turn due to a poor hold. Insert an Allen wrench into the chuck. If it is loose it can prevent movement of the teeth.
Im going to assume the DeWalt drill chuck is a hand-tighten model since the chucks that use the keys are for super old plug in drills or for a drill press.
I fixed my stuck drill chuck without taking it apart. The screw feeds inside of the drill chuck. Remove the screw in the center of the chuck. Measure the diameter of the stuck drill bit with calipers or a tape measure.

