Preheat your oven to 375°F (190°C) and generously grease a 12-cup muffin tin.

In a large mixing bowl, combine the ground beef, panko breadcrumbs, diced onion, bell pepper, minced garlic, egg, ketchup, Worcestershire sauce, smoked paprika, salt, and black pepper. Mix with your hands until just combined, being careful not to overmix.

Press the meat mixture firmly into each muffin cup, filling to the top and creating a slight dome shape.

Wrap one slice of bacon around the circumference of each meatloaf cupcake and tuck the ends underneath to secure.

Bake for 25-30 minutes, or until the meatloaf reaches an internal temperature of 160°F and the bacon is crispy.

About 10 minutes into baking, start boiling the peeled and cubed potatoes in a large pot of salted water for 15-20 minutes, until fork-tender.

While the cupcakes bake, prepare the bourbon BBQ glaze. In a small saucepan, combine the BBQ sauce, bourbon, brown sugar, and apple cider vinegar. Bring to a simmer over medium heat and cook for 5 minutes, stirring occasionally, until slightly thickened.

Remove the cupcakes from the oven and carefully drain any excess grease from the muffin tin using a spoon. Brush the tops generously with the bourbon BBQ glaze, then return to the oven and bake for another 5-10 minutes.

Drain the potatoes thoroughly and mash with warmed milk, butter, salt, and pepper until smooth and creamy.

Let the baked meatloaf cupcakes cool for 5-10 minutes before serving.

Transfer the mashed potato topping to a pastry bag or ziplock bag with the corner snipped off and pipe or spoon it onto the top of each meatloaf cupcake. Drizzle with any remaining BBQ glaze and serve warm.