Preheat the oven to 350 degrees F. Line a 9-by-4 loaf pan with parchment paper.
Combine the meatloaf mix, breadcrumbs, Cheddar, bacon, chives, parsley, eggs, onion, garlic, 1/4 cup of the ketchup, 1 tablespoon of the Worcestershire, 1 1/2 teaspoons salt and 1/2 teaspoon pepper in a large bowl. Use your hands to mix together until combined well. Transfer the mixture to prepared loaf pan. Bake the meatloaf for 30 minutes.
Meanwhile, stir the brown sugar together with the remaining 1/4 cup ketchup and 1 teaspoon Worcestershire in a small bowl.
Remove the meatloaf from the oven and brush the top and sides all over with the ketchup glaze. Bake until the glaze starts to caramelize and a thermometer inserted in the center of the meatloaf registers 160 degrees F, about 45 minutes more. Let rest for 10 minutes before slicing and serving.
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