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To prepare brine: Place sugar and 1/4 cup salt in a heatproof medium bowl. Pour in boiling water and stir to dissolve. Stir in ice cubes until melted. Add lemon quarters, rosemary sprig and sage sprig.
To butterfly & brine pork: You’re going to double butterfly the pork loin so it can be flattened, stuffed and rolled. To do so, place pork loin on a cutting board. Holding the knife blade flat, so it’s parallel to the board, make a lengthwise cut into the side of the meat just above the center, stopping short of the opposite edge so that the flap remains attached. Rotate the meat 180 degrees. Still holding the knife parallel to the cutting board, make a lengthwise cut into the side opposite the original cut, just below the center, taking care not to cut all the way through. Open up the two cuts so you have a large rectangle of meat. Cover with plastic wrap and pound to an even thickness of about 1/2 inch. Place the meat in a sealable gallon-size plastic bag and pour in the brine; turn to coat. Place in a dish and refrigerate for at least 2 hours and up to 4 hours.
To prepare rub: Combine garlic in a small bowl with 2 tablespoons oil, rosemary, sage, lemon zest, ground fennel seed and crushed red pepper.
To roast pork: Position racks in upper and lower thirds of oven; preheat to 450°F.
Remove the meat from the brine and thoroughly pat dry. Open and lay flat on a clean work surface. Spread the rub over the meat. Starting at one long end, roll it into a cylinder. Wrap prosciutto pieces around the outside (they’ll overlap a bit) and place, seam-side down, on a rimmed baking sheet.
Toss apples and fennel with oil, salt and pepper; spread in an even layer in a roasting pan.
Roast the meat on the upper rack for 10 minutes. Then place the apple mixture on the lower rack. Continue roasting, stirring the apple mixture once or twice, until an instant-read thermometer inserted into the center of the meat registers 140°F and the apples and fennel are tender, 20 to 30 minutes.
Transfer the meat to a clean cutting board and let rest for 5 minutes. Slice and serve with the apples and fennel.