Preheat the oven to 400°F. Line a baking sheet with parchment paper (we like to use a silicone baking mat).
Trim the stem of the Brussels Sprouts and cut them in half. Cut the Butternut Squash into bite-sized cubes. Cut the bacon into 1-inch pieces. If adding jalapenos, slice the jalapenos into small dials.
Place brussels sprouts, butternut squash, and jalapeno on the baking sheet. Drizzle with cooking oil, maple syrup, salt, pepper, and Italian seasoning. Mix the ingredients together to fully coat the sprouts and butternut squash. Add the bacon to the sheet pan.
Roast in the oven until the Brussels sprouts are caramelized and crispy on the outside and the bacon is crispy, about 40 minutes. Make sure to stir the ingredients halfway through.
Remove the Brussels Sprouts from the oven, drizzle with maple syrup (optional), and sprinkle with fresh ground pepper. Enjoy!