01 -
Preheat oven to 350°F.
02 -
In a large bowl, combine beef, bread crumbs, and milk. Pour the milk directly over the bread crumbs. Add 2 tablespoons ketchup, Worcestershire sauce, and steak seasoning. Set the mixture aside.
03 -
In a small bowl, slightly beat the egg. Add the egg to the meat mixture in the large bowl and combine using hands, avoiding overworking the mixture.
04 -
Gently press the meatloaf mixture into the bowl and divide it in half. Place the first half into a 7"x10" or larger baking dish and form it into a flat meatloaf. Create a rim around the outside to hold the filling.
05 -
Add the shredded cheddar cheese to the center of the formed meatloaf.
06 -
Using the remaining meat mixture, form a second layer of similar size and place it on top of the cheese-filled base. Press the edges together to seal and shape the loaf to approximately 1.5-2 inches tall.
07 -
Run warm water over your hands and smooth out any cracks on the surface of the loaf.
08 -
In a small bowl, combine 4 tablespoons of ketchup and 1 tablespoon of brown sugar. Mix thoroughly with a fork.
09 -
Evenly spread the glaze over the meatloaf, avoiding the bottom. Wrap bacon slices across the front and back of the loaf, layering remaining slices over the top. Tuck the bacon ends underneath to prevent curling.
10 -
Place the meatloaf in the oven and bake for approximately 1 hour, or until the bacon is crispy.
11 -
Remove the meatloaf from the oven and let it rest uncovered for 20 minutes. Serve and enjoy.