Preheat oven to 400 degrees. Bring a large pot of water to boil. Boil pierogies for 3 minutes, stirring constantly. Drain and let cool to the touch about 5 minutes.
Wrap each pierogy in a slice of bacon and set it seam side down on a wired rack that is on a foil-lined baking sheet (for easy clean-up later). Mix together the brown sugar and chipotle powder in a small bowl, sprinkle half of the mixture evenly over the pierogies.
Bake for 20-25 minutes, flipping them over half way through and sprinkling the remaining brown sugar mixture on top. Let cool slightly, serve with desired dipping sauce, optional.