Prepare the Pork: Preheat the oven to 375°F. Drizzle olive oil into a large baking dish. Butterfly each pork tenderloin by cutting lengthwise three-fourths of the way through (do not cut all the way through). Open like a book and place between sheets of parchment paper.
Pound for Uniformity: Use a meat mallet to pound the tenderloins to a thickness of less than 1/2-inch.
Layer the Foundation: Lay out the bacon strips on a piece of parchment paper to match the size of the tenderloins. Place the tenderloins side by side on top of the bacon. Season with salt and pepper.
Stuff and Roll: Lay the Swiss cheese slices over the pork. Top with the drained sun-dried tomatoes and blanched asparagus. Roll the tenderloins and bacon tightly together, jelly-roll style.
Glaze and Bake: Place the roll into the prepared baking dish. Stir together the ketchup and balsamic vinegar in a small bowl and brush the mixture generously over the bacon.
Roast to Temperature: Bake for 45 to 60 minutes, or until a meat thermometer inserted into the center reads 145°F.
Rest and Serve: Allow the pork to sit for 5 minutes before cutting into 1-inch slices.