Preheat the oven to 350 degrees. Prepare a loaf pan with a sling made of aluminum foil. Spritz with nonstick cooking spray.
In a small skillet or saucepan, heat olive oil over medium heat. Add the onion and bell pepper and cook for 4 to 5 minutes or until tender.
In a large stand mixer bowl, add the ground beef, crushed crackers, eggs, cheddar cheese, milk, salt, pepper, onions, and bell peppers. Beat just until mixed.
Press into the prepared loaf pan. Cook for 30 minutes in the oven.
Meanwhile, mix together the glaze ingredients.
Remove the meatloaf from the oven and cover with the glaze. Return the meatloaf to the oven and continue baking for an additional 35 to 45 minutes or until the internal temperature reaches 160 degrees.
Allow the meatloaf to rest for 10 minutes in the loaf pan before lifting from the loaf pan and slicing.