Cut each strip of bacon in half, then lay flat on a rimmed baking sheet lined with parchment paper.
In a small bowl, combine the brown sugar and chipotle chili powder. Spoon 1 teaspoon of the brown sugar mixture onto each piece of bacon, then spread it out using the back of a spoon or your fingers to cover the length of it.
Starting at one end of each bacon strip, wrap the shrimp tightly inside the bacon, securing the end with a toothpick.
Bake at 375°F for 15 minutes, then broil on high for an additional 3 minutes, watching carefully to prevent burning.
Remove the baking sheet from the oven, transfer shrimp to a serving plate, and drizzle with honey and fresh cracked pepper. Serve with additional honey for dipping.