Adjust the oven rack to the center position and preheat the oven to 400°F (204°C).

Line a baking sheet with foil and place a wire rack on top.

Spray the rack with nonstick cooking spray.

Place 5 slices of bacon spaced evenly apart on the pan.

Roast until the bacon just begins to shrink and turns a slightly red color, but is still flexible, about 5 minutes, depending on thickness. The bacon should not be completely crispy, otherwise, it will break when wrapping around the asparagus.

Remove the bacon from the oven and brush with the maple syrup mixture on both sides. Roast the bacon for 3 more minutes.

Allow the bacon to cool until it’s easy to handle with your fingers. Divide the asparagus into five even-size bundles.

On a cutting board, wrap one slice of the par-cooked bacon overlapping over the length of the asparagus spears.

Secure the bacon with a toothpick. Carefully place the bundles on the baking rack. Generously brush the maple syrup mixture over the bacon-wrapped asparagus spears on both sides.

Lightly season each bundle with salt and pepper.

Roast the asparagus bundles for 10 minutes, remove from the oven and brush the maple mixture over just the bacon.

Roast for 5 minutes, or until the bacon is browned and crispy, and the asparagus is tender.

Remove the toothpicks and serve the bacon wrapped asparagus hot.