Preheat your oven to 350 degrees. Place oven rack in center.
Remove the pork tenderloin from packaging and pat dry. Salt and pepper all sides of the tenderloin. Set aside.
Lay 10 to 12 strips of bacon on a cutting board. You want the length of the bacon horizontally to be about as long as your tenderloin.
Place half of the bacon strips vertically, and the other half horizontally. Lift each slice of bacon and weave them together in a cross-hatch pattern as shown in the picture above.
Heat a large cast iron skillet on the stove top to medium-high. When it is hot, add the oil and swirl it around the pan. Quickly sear the pork tenderloin on all sides. You want a light brown, then remove it. Set the pan to the side for later.
Place the pork tenderloin in the center of the weaved bacon strips. Carefully fold the bacon over the pork, wrapping it. Grasping the tenderloin with both hands, quickly flip it so the bacon is tucked underneath.
You can secure the bacon with toothpicks if you prefer.
With a large spatula, carefully transfer the bacon wrapped pork tenderloin back to the cast iron skillet. Place in the oven and bake uncovered for 35 - 40 minutes.
You do not want to overcook the tenderloin. Cooking times will vary based on your oven and thickness of pork. Use a meat thermometer to ensure the pork is properly cooked.
During the cooking process, brush and baste the tenderloin with the cherry barbecue sauce (below) and spoon the pan drippings over the top. Repeat until the sauce is rich and sticky on the bacon.
Remove from the oven and cover lightly with foil. Let rest 10 minutes before slicing.