Step 1: Preheat your oven to 375°F (190°C).
Step 2: Grease a standard 12-cup muffin tin or line it with silicone or paper muffin liners for easy removal.
Step 3: In a large mixing bowl, combine the ground beef, breadcrumbs, milk, finely chopped onion, minced garlic, egg, ketchup, Worcestershire sauce, Italian seasoning, salt, and pepper.
Step 4: Using your hands, gently mix all ingredients until just combined. Be careful not to overmix, as this can lead to a tough meatloaf.
Step 5: Divide the meatloaf mixture evenly among the prepared muffin cups, filling each about three-quarters full.
Step 6: Lightly press the mixture down to form uniform cupcake shapes. You can also create a small indent in the center to help them cook evenly.
Step 7: Bake for 20-25 minutes, or until an instant-read thermometer inserted into the center of a meatloaf cupcake registers 160°F (71°C).
Step 8: Remove from the oven and let the meatloaf cupcakes cool slightly in the muffin tin before transferring them to a wire rack. This helps them firm up and makes them easier to handle.
Step 9: While the meatloaf cupcakes are cooling, combine your prepared mashed potatoes, softened butter, and heavy cream (or milk) in a bowl.
Step 10: Using a hand mixer or a sturdy whisk, whip the potato mixture until it is light, fluffy, and smooth.
Step 11: Season the whipped potatoes to taste with salt and freshly ground black pepper.
Step 12: Once the meatloaf cupcakes have cooled enough to handle, spoon or pipe the whipped potato topping onto each meatloaf. For a true cupcake look, use a piping bag with a star tip!
Step 13: Garnish each meatloaf cupcake with a diced cherry tomato and a sprinkle of fresh chives or parsley.