Cheese-Filled Meat Loaf

Step 1
Preheat oven to 350 degrees F (175 degrees C). Chop 4 bacon strips; set remaining 4 bacon strips aside.

Step 2
Cook chopped bacon in a large skillet over medium heat, stirring often, until bacon is browned and crisp, 8 to 10 minutes. Set chopped bacon aside.

Step 3
Lightly mix ground beef, bread crumbs, beaten egg, garlic, 1 teaspoon Worcestershire sauce, salt, and black pepper together in a bowl until thoroughly combined. Spread meat mixture out on a piece of waxed paper, forming a rectangle about 10 inches square. Spread Cheddar cheese and cooked chopped bacon over the meat, leaving a 1/2-inch edge all around. Carefully lift an edge and roll the meat around the filling. Place into a loaf pan with the seam side down.

Step 4
Bake meat loaf in the preheated oven until hot and beginning to brown, about 30 minutes. Mix ketchup, brown sugar, pineapple, and 1 teaspoon Worcestershire sauce together in a bowl, stirring to dissolve brown sugar. Remove meat loaf from oven and place remaining 4 bacon strips onto meat loaf, weaving them together. Spread pineapple mixture over woven bacon and top of loaf.

Step 5
Return meat loaf to oven and bake until bacon topping is crisp and pineapple mixture has baked into a glaze, about 20 more minutes. An instant-read meat thermometer inserted into the center of the meat loaf should read 160 degrees F (70 degrees C).