Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or nonstick foil to prevent sticking and make cleanup easier.
Heat the extra virgin olive oil in a medium nonstick pan over medium heat until hot but not smoking. Add the finely diced onion and saute until translucent, about 3-5 minutes. Stir in the minced garlic and continue to saute for another 2 minutes. Set the mixture aside and allow it to cool to room temperature.
In a large bowl, add the meatloaf mix, Dijon mustard, Worcestershire sauce, 1/3 cup ketchup, panko bread crumbs, kosher salt, eggs, whole milk, ground black pepper, and chopped fresh parsley. Once the onion and garlic mixture is cooled (from Step 2), add it in. Mix thoroughly, ideally using your hands for best texture and even blending. I find using my hands helps everything come together without overworking the mixture.
Form the meatloaf mixture (from Step 3) into a rectangular loaf shape and place it on the prepared baking sheet. In a small bowl, whisk together 2 tablespoons ketchup with the brown sugar. Brush this glaze generously all over the top and sides of the meatloaf. Lay the strips of thick-cut bacon across the loaf from short end to short end, overlapping slightly, until fully covered. Make sure all surfaces are covered for the best result.
Transfer the loaf to the oven and bake for about 1 hour to 1 hour and 15 minutes, rotating the pan once or twice during baking to ensure even cooking. When done, remove the meatloaf from the oven and tent it with foil. Let it rest for about 10 minutes before slicing to help keep it moist and allow the juices to settle. I always give my meatloaf this short rest—it makes slicing cleaner and the texture much better.