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Start the Traeger on Smoke with the lid open until the fire is established (about 5 minutes). Preheat, lid closed, to High heat (10 to 15 minutes).
Slice the bacon in half crosswise. Wrap each tomato with a half slice of bacon and secure with a wooden toothpick.
Place the tomatoes on a large foil-lined baking sheet and sprinkle them with cracked black pepper.
Cook the tomatoes on the Traeger for about 25 minutes or until the bacon has rendered and tomatoes are bursting.
Remove the tomatoes and serve them warm with a drizzle of balsamic vinegar and fresh basil, if desired. Enjoy!