Pork Loin with Spiced Butternut Squash

Preheat oven to 425 degrees.
In a large bowl, stir together 3 tablespoons olive oil, sugar, water, chile powder, cumin and cinnamon. Add squash and toss to coat. Set aside.
Generously season pork with salt and pepper.
In a large skillet, heat remaining olive oil over high heat. Cook pork on all sides until deep golden brown, about 10 minutes total. Place pork on a rimmed baking sheet. Pour oil from skillet over sheet and spread evenly.
Arrange squash wedges around pork and brush pork with remaining sugar mixture from the bowl. Roast until pork is cooked to 135 degrees, about 40 minutes, brushing pork with sugar mixture and turning squash every 15 minutes. Test pork with folk and let rest 10 minutes before serving.