Preheat Oven: Preheat oven to 450 °F.
Prepare Glaze: In a small saucepan over medium-high heat, combine maple syrup, brown sugar, 1 Tablespoon Dijon mustard, apple cider vinegar, and cayenne. Whisk often. Once it starts to boil, turn heat down and let it simmer for 2-3 minutes until it thickens into a glaze. Remove from heat and set aside.
Prepare Garlic Rub: In a small bowl, whisk remaining 1 Tablespoon Dijon with olive oil, garlic, salt, and pepper.
Prepare Tenderloin: If ends of the tenderloin are thin, tuck them under so the pork cooks evenly. Brush garlic rub mixture all over.
Wrap in Bacon: Wrap the bacon slices around the tenderloin, overlapping slightly and keeping them snug so they don’t slide off. Set it seam-side down in a cast iron skillet or baking dish. If needed, secure the bacon with toothpicks (remove before serving). Brush half the glaze over the bacon.
Roast: Bake for 20-25 minutes, or until internal temperature reaches about 140°F.
Broil to Crisp: Remove the pan from the oven and switch the oven to broil. Brush the remaining glaze over the bacon, then return the pan to the oven and broil for 1-3 minutes, watching closely since the glaze can brown fast.
Rest and Slice: Let pork rest for 10-15 minutes before slicing so it stays juicy.