Preheat oven to 400 F. Place rack at center. Line a rimmed baking sheet with foil or parchment paper and brush lightly with oil or spray with cooking spray.
Brush the pork evenly with olive oil. Sprinkle all over with ½ teaspoon kosher salt and ¼ teaspoon freshly ground black pepper.
If your tenderloin has a thin tail, tuck it under so the pork cooks evenly. Wrap or wind the meat evenly with two pieces of bacon, one at a time, securing at center and end (including the tucked under tail if you’ve done that) with toothpicks. Count your toothpicks so when you serve the meat, you’ll know you removed them all. Place the pork on one side of the lined baking sheet.
Score the halved sweet potatoes using a paring knife (cut a crosshatch pattern about 1/8-inch into the flesh). Brush the cut side with a little olive oil and sprinkle each generously with salt, pepper, paprika, and chili powder. Place potatoes cut side down, an inch or so apart from one another, on the other side of the baking sheet.
Roast about 20 minutes or until pork registers 140 F on an instant read thermometer. Remove the pork to a cutting board to rest and return the pan with the potatoes back to the oven for another 10 minutes or until they're tender. A small sharp knife should go in and out of them easily when they're done. Slice the meat thinly (count the toothpicks!) and serve with the hot sweet potatoes. (If you like your pork well-done, leave it in the oven to continue cooking for the last 10 minutes with the potatoes.)Store leftovers tightly wrapped in the fridge for up to three days. While the meat will freeze well for up to two months, don’t freeze the sweet potatoes.