Preheat oven to 375°F. Grease a 9x5-inch loaf pan or line with parchment.
Whisk eggs, milk, 1/3 cup ketchup, and Worcestershire in a large bowl.
Stir in crushed crackers and let sit 2 minutes to hydrate.
Add beef, onion, bell pepper, garlic powder, salt, and pepper. Mix gently until just combined.
Shape into a loaf and set in the prepared pan, smoothing the top.
Combine 1/2 cup ketchup, brown sugar, mustard, and vinegar to make the glaze.
Bake 35 minutes. Brush the top with about half the glaze.
Return to oven 20–25 minutes, until the center reaches 160°F.
Rest 10 minutes. Slice and serve with the remaining glaze.