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Heat a large high-sided skillet over medium-high heat and add the olive oil.
Add the ground beef and chopped onion. Season with salt and pepper. Cook, breaking up the beef, until browned and the onions are soft, about 5–7 minutes.
Stir in the smoked paprika, chili powder, garlic powder, onion powder, and oregano. Cook for 1 minute to bloom the spices.
Add the uncooked pasta, beef broth, milk, Worcestershire, mustard, ketchup, and (optional) pickle brine. Stir well to combine.
Bring to a gentle boil, then reduce heat to medium. Cover and cook for 10–12 minutes, stirring occasionally, until the pasta is cooked and the sauce has thickened.
Remove from heat and stir in the shredded cheddar cheese until melted and creamy.
Taste and adjust seasoning with additional salt, pepper, or pickle brine.
Serve topped with fresh parsley, green onions, or crispy shallots.