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Step 1
Prepare the seasoning: Mince the garlic finely on a large cutting board, then sprinkle with a pinch of kosher salt. Use the knife to press and scrape the minced garlic against the cutting board until you have a smooth paste. Transfer the garlic paste to a small mixing bowl and zest in the orange (save the fruit for later). Add the rosemary, paprika, cinnamon, 1/2 teaspoon black pepper, 2 teaspoons kosher salt, and 3 tablespoons olive oil. Mix into a paste.
Step 2
Season the pork: Pat the pork loin dry with paper towels. Use a sharp knife to slide under the thin white layer of silverskin and remove it (leave the thicker layer of fat, called the fat cap, on top as it will keep the meat juicy and flavorful as it roasts). Spread the paste all over the pork loin. Set aside at room temperature while preparing the squash and apples, or refrigerate it overnight if you have the time.
Step 3
Preheat the oven: Arrange a rack in the center of the oven and preheat it to 425°F.
Step 4
Prep the squash and apples: In a large bowl, season the butternut squash and apple with the remaining 2 tablespoons olive oil, 1/2 teaspoon kosher salt, and 1/4 teaspoon black pepper.
Step 5
Roast: Set the pork loin in the center of a large roasting pan. Arrange the squash and apples around the pork. Slice the zested orange in half and squeeze the juice from half of the orange over the pork, squash, and apples. Roast for 25 minutes. Reduce the heat to 350°F and roast until the internal temperature of the pork registers 145°F, 30 to 40 minutes.
Step 6
Rest: Remove the pork from the oven and cover the loosely with foil. Let it rest for 15 to 20 minutes.
Step 7
Slice and serve: Cut the pork loin crosswise into 3/4-inch-thick slices. Serve with the roasted squash, apples, and a drizzle of the pan drippings over top.