Bring a pot of salted water to a boil and blanch the Brussels sprout halves for 3 minutes, until just bright green and slightly softened at the edge of a fork.
Drain the sprouts and run them under cold water to stop the cooking, then pat completely dry.
Preheat the oven to 400°F and line a baking sheet with foil.
Wrap a half-piece of bacon around each sprout half and secure with a toothpick through the center.
Arrange the wrapped sprouts cut-side up on the baking sheet, leaving space between each one.
Whisk together the maple syrup, Dijon, olive oil, black pepper and chili flakes in a small bowl.
Brush half the glaze over the sprouts and roast for 20 minutes.
Brush with the remaining glaze, then broil for 2 to 3 minutes, watching closely, until the bacon is crisp and the edges are deep golden.
Good to Know
Blanch and wrap the sprouts up to a day ahead, refrigerate raw on the sheet, then glaze and roast straight from cold, adding about 5 extra minutes.