Directions

1. Preheat oven to 425. In a large bowl, stir together 3 tablespoons oil, sugar, chile powder, cinnamon, cumin, and 2 tablespoons water. Add squash and toss to coat. Set aside.
2. Generously season pork with salt and pepper. Heat a cast-iron skillet or other heavy pan over high. Add 1 tablespoon oil and swirl to coat. Cook pork on all sides until deep golden brown, about 10 minutes total. Place pork on a rimmed baking sheet; pour oil from skillet onto sheet and spread evenly.
3. Arrange squash around pork. Brush pork with sugar mixture from bowl. Bake until pork is cooked through (an instant-read thermometer inserted in center should register 135 degrees), 40 to 45 minutes, brushing meat with sugar mixture and turning squash every 15 minutes. Tent pork with foil and let rest 10 minutes before slicing.