Preheat oven to 350°F. Line a baking sheet with parchment.
Place bacon on the sheet and bake for 12–15 minutes until mostly cooked but still flexible. Cool on paper towels.
Open cinnamon rolls, separate, and let sit at room temp for 5 minutes. Set icing aside.
Simmer brown sugar and ¼ cup maple syrup in a saucepan over medium-low heat until thickened (2–3 mins).
Dip bacon in the glaze, coating both sides. Let excess drip off.
Line or grease a 9-inch round dish. Spread half of the remaining glaze on the bottom.
Wrap each cinnamon roll with a glazed bacon slice. Trim if needed. Arrange in the dish with space between each.
Drizzle leftover glaze lightly over and around the rolls (avoid soaking the tops).
Bake for 25–30 mins until rolls are golden and bacon is crisp. Toothpick should come out clean.
Mix icing with 1 tbsp maple syrup and drizzle over warm rolls. Garnish with extra crumbled bacon if desired.