Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper for easy cleanup.
Place the trimmed and halved Brussels sprouts on the prepared baking sheet. Drizzle them with olive oil and season with salt, pepper, and garlic powder. Toss to coat evenly.
Roast in the preheated oven for about 15 minutes, or until the Brussels sprouts begin to caramelize and turn golden brown at the edges.
While the Brussels sprouts are roasting, cook the chopped bacon in a skillet over medium heat until crispy. Use a slotted spoon to transfer the bacon to a paper towel-lined plate to drain.
In the same skillet with the remaining bacon fat, add the chopped pecans. Toast them for 2-3 minutes, stirring frequently until they're fragrant and slightly browned. Remove from heat and set aside.
Once the Brussels sprouts are roasted, remove them from the oven. Add the crispy bacon, toasted pecans, and sugar-free dried cranberries to the baking sheet with the Brussels sprouts.
In a small saucepan, melt the unsalted butter over low heat and stir in the apple cider vinegar. Once combined, drizzle the butter mixture over the Brussels sprouts and toppings on the baking sheet. Toss everything together to distribute the flavors.
Return the baking sheet to the oven and roast for an additional 5 minutes, allowing the flavors to meld and the Brussels sprouts to get a final crisp.
Remove from the oven and serve immediately, garnishing with additional salt and pepper if desired.