I haven't tried this with garden gloves yet, but when I wear a fingertip hole in other gloves, I'll wrap the tip of that finger with tape (masking tape, duct tape, or Gorilla Tape). That lasts forever, but it is slick, and reduces the gripping power.
When roots need a stronger tug then my fingers can deliver (the usual case unless it's a well-amended bed), I usually go after the roots with a kitchen knife or bayonet . If I'm not just decapitating them with a scuffle-hoe, I'll go as deep as I can.
DO NOT DEFY THE COREY-GARDENER, MR. WEED!