5 garlic cloves, peeled
1 tablespoon freshly ground black pepper
1 tablespoon ground allspice
1 tablespoon kosher salt
1 tablespoon light brown sugar
3 tablespoons rosemary leaves, plus 6 sprigs
2 tablespoons extra-virgin olive oil, plus more for brushing
2 large pork tenderloins (about 3 pounds)
12 ounces thin-sliced bacon (about 12 slices)
Cranberry sauce (for serving; optional)
Pulse garlic, pepper, allspice, salt, brown sugar, 3 Tbsp. rosemary leaves, and 2 Tbsp. oil in a food processor until a paste forms. Alternatively, finely chop garlic and 3 Tbsp. rosemary leaves and transfer to a small bowl; stir in pepper, allspice, salt, brown sugar, and 2 Tbsp. oil.
Rub garlic paste all over pork. Let sit at least 30 minutes, or cover and chill up to overnight.
Arrange a rack in top third of oven; preheat to 425°F. Wrap each tenderloin in bacon, working in a spiral from top to bottom and letting each layer overlap slightly, until completely covered (about 5 bacon slices per tenderloin). Secure any exposed bacon slice ends with toothpicks.
Arrange 6 rosemary sprigs on a rimmed baking sheet. Arrange pork over. Brush tops of tenderloins with oil. Roast pork until an instant-read thermometer inserted into thickest part registers 140°F for medium-rare (about 20 minutes) or 145° for medium, (about 25 minutes). Transfer to a cutting board and let rest 10 minutes before slicing. Serve with cranberry sauce if desired.