Preheat your oven to 400°F (205°C). Pat the pork tenderloin dry with paper towels. Dry meat sears better and helps the bacon crisp.
Trim any silver skin from the tenderloin if needed.
Season the pork with salt, pepper, smoked paprika, and garlic powder on all sides.
Lay the bacon strips slightly overlapping on a cutting board to form a rectangle about the length of the tenderloin. Place the pork at one end and roll it up, wrapping the bacon around as you go. Tuck the ends under.
Use a couple of toothpicks if needed to keep the seams secure.
In an oven-safe skillet, heat the olive oil over medium-high. When it’s hot and shimmering, place the bacon-wrapped tenderloin seam-side down. Sear for 2–3 minutes per side until the bacon begins to brown. Rotate to sear all around.
Whisk together the glaze ingredients: maple syrup, Dijon, minced garlic, and vinegar.
Brush a thin layer over the bacon after searing.
Transfer the skillet to the oven. Roast for 12–18 minutes, depending on thickness, brushing once more with glaze halfway through. Start checking early.
Use an instant-read thermometer to check for doneness.
For juicy, slightly pink pork, pull it at 140–145°F (60–63°C). The bacon should be browned and slightly crisp.
Move the tenderloin to a cutting board and let it rest 5–10 minutes. Resting keeps the juices in the meat instead of on the board.
Slice into 1/2- to 3/4-inch medallions.
Spoon any pan juices over the top. Serve with roasted vegetables, mashed potatoes, or a crisp salad.