Cheese-Filled Meat Loaf

Preheat oven to 350°F (175°C). (5 minutes)

Chop 4 bacon slices into 1/4-inch pieces. Reserve the remaining 4 bacon slices for the topping.

In a large skillet over medium heat, cook the chopped bacon, stirring frequently, until crisp and rendered, about 8-10 minutes. Remove with a slotted spoon and set aside, reserving the bacon fat in the pan. (10 minutes)

In a large bowl, gently combine the ground beef, bread crumbs, beaten egg, minced garlic, 1 teaspoon Worcestershire sauce, salt, and pepper. Mix just until combined; avoid overmixing to prevent a tough meatloaf.

On a large sheet of parchment paper, pat the meat mixture into a 10-inch square. Sprinkle the shredded Cheddar cheese evenly over the meat, followed by the cooked bacon pieces, leaving a 1/2-inch border around the edges.

Carefully lift one edge of the parchment paper and roll the meat tightly around the cheese and bacon filling, forming a log. Pinch the seam to seal and transfer the meatloaf, seam-side down, into a loaf pan.

Bake in the preheated oven for 30 minutes, or until the meatloaf is beginning to brown.

While the meatloaf bakes, prepare the pineapple glaze. In a small bowl, whisk together the ketchup, brown sugar, drained crushed pineapple, and remaining 1 teaspoon Worcestershire sauce until well combined.

Remove the meatloaf from the oven. Arrange the remaining 4 bacon slices across the top of the meatloaf, weaving them together for a decorative effect. Brush the pineapple glaze generously over the woven bacon and the entire surface of the meatloaf.

Return the meatloaf to the oven and continue baking for another 20 minutes, or until the bacon is crisp, the glaze is caramelized, and an instant-read thermometer inserted into the center of the meatloaf registers 160°F (70°C). (20 minutes)

Remove from the oven and let rest for 10 minutes before slicing and serving. This allows the juices to redistribute, resulting in a more tender and flavorful meatloaf. (10 minutes)