1. Preheat oven to 350 degrees.
2. Season the pork with salt and pepper. Lay out strips of bacon slightly
overlapping and roll the tenderloin in the bacon, securing along the
sides with toothpicks.
3. Heat the oil in a large cast iron skillet, or other oven-proof skillet,
over medium-high heat until shimmering. Add the bacon-wrapped
tenderloin and sear undisturbed until deep caramel brown, 4-6
minutes. Flip the tenderloin and sear until all sides are browned.
4. Transfer the skillet to the oven and cook the tenderloin until the center
registers 145°F, approximately 15 to 20 minutes.
5. In a small saucepan, bring all ingredients to a boil, lower the
temperature and simmer 5-10 minutes until sauce thickens.
6. Remove from the oven, loosely tent with aluminum foil, and set aside
to rest for 5-10 minutes to allow the tenderloin to finish cooking and
for the juices to redistribute into the meat. Remove the toothpicks and
cut crosswise into 1/4- to 1/2-inch-thick slices. Serve with the cherry
sauce and enjoy!