1Heat the oven to 500°F and arrange a rack at the top.
2Coat the tenderloin with 1 teaspoon of the olive oil and season with salt and a generous amount pepper. Wrap the bacon around the tenderloin in a spiral so it completely covers the meat. Place on a baking sheet and roast until the bacon just begins to render, about 10 minutes.
3Meanwhile, core the apples, slice into 6 wedges each, and place in a large bowl. Add the remaining 3 teaspoons olive oil, measured salt, and pepper. Toss until well coated.
4Scatter the apples around the tenderloin without allowing them to touch each other or the pork, and roast until the bacon is light brown, the underside of the tenderloin is browned and the meat registers 150°F on a digital thermometer, and the apples are knife tender, about 10 minutes more.
5Set the oven to broil and cook the tenderloin until the apples begin to brown, the bacon is golden brown, and the pork reaches 155°F to 160°F. Let rest at least 5 minutes before serving.