Heat 1 tbsp of olive oil in a large skillet over medium-high heat. Add 1 lb ground beef and diced onion, breaking apart the meat, and cook for 5 to 7 minutes until browned.
Stir in 3 minced garlic cloves and all seasonings, cooking for 1 minute until fragrant.
Add 1 tbsp of tomato paste and 1 tbsp of Worcestershire sauce, cooking for 1 to 2 minutes to caramelize.
Pour in 2 cups beef broth, 1 cup whole milk, and 1 can undrained diced tomatoes. Stir in 2 cups of dry elbow macaroni.
Cover and reduce heat to medium-low, simmer for 12 to 15 minutes stirring every 4 to 5 minutes until pasta is tender.
Remove from heat, add 2 cups of shredded cheddar cheese gradually, stirring until melted and creamy. Adjust seasoning if needed and serve immediately.