Preheat the oven to 400°F and line a sheet pan with foil. Spread the onions and bell peppers on the pan in a single layer.

Whisk the tomato paste and two tablespoons of olive oil in a small bowl. Pour the mixture over the veggies and stir or lightly toss them to coat them evenly.

Slice the top of the head of garlic off – just enough to expose the top of most of the cloves. Place the garlic on a piece of foil and drizzle 1 teaspoon of oil over the top. Loosely wrap the garlic in the foil and place it on the sheet pan with the other veggies.

Roast the vegetables for 40 to 45 minutes or until they are soft and lightly charred around the edges. Cool them on the pan.

While the veggies cool, brown the ground beef in a non-stick skillet over medium heat. While it cooks, add the Italian seasoning, salt, and pepper. Break up the beef as it cooks.

Once the ground beef is browned, add the wine (or vinegar, if using), tomato sauce, Worcestershire sauce, and brown sugar. Stir to combine.

Unwrap the garlic and squeeze the cloves out onto a cutting board. Place the roasted peppers and onion on the board, too. Finely chop the garlic and veggies with a sharp knife or, if you want a shortcut, chop them in a food processor.

Add the chopped vegetables to the ground beef mixture in the pan. Stir and bring the sloppy joes to a simmer. Simmer the mixture for 20 to 30 minutes or until thickened.