Preheat oven to 375°F (190°C). In a small bowl combine 2 Tbsp. brown sugar, Jamaican jerk seasoning, salt, pepper, and orange zest. Rub tenderloins with seasoning mixture.
Heat olive oil in a skillet over high heat and when hot add tenderloins. Sear each side for 1 minute, until lightly browned. Remove tenderloins from skillet and put in roasting pan.
Dredge bacon in 1 Tbsp. brown sugar and top each tenderloin with 2 pieces of bacon. Add pan to pre-heated oven and roast for 20-30 minutes until a meat thermometer inserted into the roast reads 150 degrees F, then remove from oven.
Half way through the pork's roasting time, deglaze skillet that pork was seared in with vinegar over medium heat. add dijon, orange juice, and brown sugar and simmer for about 3 minutes until sauce starts to reduce.
Spoon sauce over roasts and broil roasts on low for 2-5 minutes to crisp bacon and raise temperature to 155 - 160 degrees. Crack the oven door open while broiling and watch to prevent tenderloins from burning.
Remove pork from oven and let sit 10 minutes before carving to allow pork to fully cook and flavors to meld.