If the squash is too hard to cut through, put it in the microwave for a couple of minutes! Place the whole raw squash on a microwave-safe plate and microwave it for 2 to 3 minutes. Warming the delicata in the microwave will tenderize the skin just enough for your knife to go through easily. Be sure to wear oven mitts when removing the squash from the microwave! This hack works for all winter squash. the whole raw squash into the microwave for 2 to 3 minutes. This will soften the skin enough for you to cut through easily. Wear oven mitts when removing the delicata squash from the microwave.