Working one at a time on a flat surface, place a tater tot on a piece of bacon. Gently cut a slit down the center of each tater tot, adding a cheese square into the opening.
Wrap each tater tot in bacon, securing with a toothpick if needed. Repeat with remaining bacon pieces, tater tots and cheese squares.
Dredge each bacon wrapped tater tot in brown sugar, pressing to coat.
for the oven
Preheat oven to 400 degrees F. Line a baking sheet with parchment paper or a silicone baking mat; set aside.
Place bacon wrapped tater tots seam side down in a single layer onto the prepared baking sheet. Place into oven and bake until the tater tots are cooked through and bacon is crispy, about 20-25 minutes, using metal tongs to turn at halftime.
for the air fryer
Preheat air fryer to 400 degrees F. Lightly oil the air fryer basket or coat with nonstick spray.
Place bacon wrapped tater tots seam side down in a single layer onto the prepared air fryer basket. Place into air fryer and air fry until the tater tots are cooked through and bacon is crispy, about 12-15 minutes, shaking the basket at halftime.
Serve immediately, garnished with parsley, if desired.