Preheat the oven to 375°F and line a rimmed baking sheet with parchment paper or aluminum foil and spray with cooking spray (if using aluminum foil). Set aside.
In a small saucepan, whisk together the brown sugar, Dijon mustard, apple cider vinegar, pepper and chili powder, bringing to a simmer. Whisk until smooth and mixture starts to bubble. Be mindful that it could boil over (sugar does this). When sugar is dissolved, remove from the heat.
On a cutting board or clean work surface, wrap each 1-inch piece of kielbasa in a half slice of bacon, placing seam-side down on the prepared baking sheet.
Baste the bites with the prepared brown sugar glaze and place into the oven, baking for 40-45 minutes, basting every 10-15 minutes. Remove when bacon edges start to char bites are a deep brown.
Remove and allow to cool for 10-15 minutes before serving.
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