Heat the olive oil in a large nonstick skillet over medium-high heat. Add chopped onion, chopped carrot, dried oregano, and minced garlic; sauté 2 minutes. Cool.
Combine onion mixture, ½ cup ketchup, and the remaining ingredients except cooking spray in a large bowl.
Spoon the meat mixture into 12 muffin cups coated with cooking spray. Top each with 2 teaspoons ketchup. Bake at 350° for 25 minutes or until a thermometer registers 160°. Let stand for 5 minutes.
While the meatloaf is cooking, make the mashed potatoes. Place potato in a saucepan; cover with water. Bring to a boil; cover, reduce heat, and simmer 10 minutes or until tender. Drain. Put potatoes into a ricer for best results. Return potato to pan. Add milk and remaining ingredients; stir with a spoon to desired consistency. If they are not creamy enough for you, add up to ¼ cup more milk – although they need to be stiff enough to pipe on top.
Put the potatoes into a pastry bag with a wide star tip and pipe the mashed potatoes on top of the meatloaf. Sprinkle with bacon crumbles and chopped chives.
Recipe by Recipes to Try at https://recipestotry.ca/meatloaf-cupcakes/