Preheat your oven to 375°F (190°C). Lightly grease a standard 12-cup muffin tin with cooking spray or a thin layer of oil to prevent sticking. Set the prepared pan aside while you prepare the meatloaf mixture.
Place the turkey bacon in a skillet over medium heat and cook for about 5 minutes, turning occasionally, until it becomes slightly cooked but remains soft and flexible. It should not be fully crispy because it will continue cooking in the oven. Transfer the turkey bacon to a paper towel-lined plate and let it cool for a few minutes.
In a large mixing bowl, combine the ground beef, almond flour, eggs, finely diced onion, minced garlic, shredded cheddar cheese, Worcestershire sauce, half of the sugar-free BBQ sauce, smoked paprika, garlic powder, onion powder, salt, black pepper, and chopped parsley. Mix gently with clean hands or a large spoon until everything is evenly incorporated. Be careful not to overmix, as this can make the meatloaf dense instead of tender.
Line each muffin cup with one slice of the partially cooked turkey bacon, allowing the ends to overlap slightly over the edges of the cup. The turkey bacon will help hold the meatloaf together while adding delicious smoky flavor and crisp edges.
Divide the meat mixture evenly among the prepared muffin cups. Press it down gently so each cup is filled, but avoid packing it too tightly. A light touch helps keep the meatloaf moist and juicy after baking.
Brush the tops of the meatloaf cupcakes generously with the remaining sugar-free BBQ sauce. This creates a flavorful glaze that caramelizes beautifully as the cupcakes bake.
Bake for 25 to 30 minutes, or until the meatloaf reaches an internal temperature of 160°F (71°C). The turkey bacon should be lightly browned around the edges, and the BBQ glaze should appear glossy and slightly caramelized.
While the meatloaf cupcakes are baking, steam the cauliflower florets until they are very tender, about 10 to 12 minutes. Drain the cauliflower thoroughly to remove as much moisture as possible, then transfer it to a food processor with the butter, cream cheese, heavy cream, salt, and pepper. Blend until completely smooth, creamy, and fluffy, stopping to scrape down the sides if necessary.
Once the meatloaf cupcakes are finished baking, let them rest in the muffin tin for about 5 minutes. Carefully remove each one using a spoon or small spatula and transfer them to a serving platter.
Spoon the warm cauliflower mash into a piping bag fitted with a large star tip and pipe generous swirls onto each meatloaf cupcake to resemble frosting. If you don't have a piping bag, simply spoon the mash over the tops and spread it gently with the back of a spoon. Garnish with freshly chopped parsley, if desired, and serve immediately while warm.