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In a large pot, heat olive oil over medium heat. Add ground beef, breaking it up as it cooks. Season with salt and pepper.
Add chopped onion and garlic to the pot, cooking for 2-3 minutes until softened.
Stir in diced tomatoes, beef broth, Worcestershire sauce, and elbow macaroni. Bring to a boil, then reduce heat to low.
Cover and simmer for 10-12 minutes, stirring occasionally, until the macaroni is tender and the liquid is mostly absorbed.
Stir in milk and cheddar cheese, mixing until the cheese melts and the sauce is smooth.
Taste and adjust seasoning with salt and pepper if needed.
Serve hot, garnished with extra cheese or chopped herbs if desired.