Step 1: Prep the Water Chestnuts
Drain the water chestnuts in a colander and rinse thoroughly under cold water. Pat them completely dry with paper towels. If using the optional marinade, place the dried water chestnuts in a small bowl with soy sauce and let them sit for 15-30 minutes, then drain and pat dry again.

Step 2: Prepare Your Baking Setup
Preheat your oven to 375°F. Line a rimmed baking sheet with aluminum foil for easy cleanup. If you have a wire cooling rack that fits inside your baking sheet, place it on top of the foil – this is optional but helps create crispier bacon. Soak wooden toothpicks in water for 10 minutes to prevent burning.

Step 3: Cut the Bacon
Lay bacon strips on a cutting board and cut each slice in half. If your water chestnuts are particularly small or your bacon slices are long, you may want to cut them into thirds instead. You want just enough bacon to wrap around each water chestnut once with a slight overlap.

Step 4: Wrap the Water Chestnuts
Take one water chestnut and wrap it with one piece of bacon, securing with a toothpick pushed all the way through. The toothpick should go through the bacon overlap, the water chestnut, and ideally through the other side of bacon to hold everything securely. Repeat with remaining water chestnuts and bacon pieces.

Step 5: Coat with Brown Sugar
Pour the brown sugar into a shallow dish or plate. Roll each bacon-wrapped water chestnut in the brown sugar, coating all sides generously. Press gently to help the sugar adhere to the bacon. Place sugar-coated bites on your prepared baking sheet, seam-side down, spacing them about 1 inch apart.

Step 6: Bake
Place the baking sheet in the preheated oven and bake for 30-35 minutes, turning the bites over halfway through cooking (around the 15-minute mark). They’re done when the bacon is crispy and browned and the sugar has caramelized into a beautiful glaze.

Step 7: Drain and Cool Slightly
Remove from the oven and let the bacon bites rest for 2-3 minutes. If you didn’t use a wire rack, you may want to transfer them to a paper towel-lined plate briefly to drain excess grease. Don’t let them cool too long or the sugar will harden and they’ll stick.

Step 8: Serve
Transfer the bacon wrapped water chestnuts to a serving platter while still warm. The caramelized sugar coating should be glossy and sticky. Serve immediately while hot for the best texture and flavor.