Heat olive oil in a large pot or deep skillet over medium-high heat.
Add ground beef to the pot and cook, breaking it apart with a spoon, until browned and cooked through, about 5-7 minutes.
Drain excess fat if necessary, then add minced garlic, dried Italian seasoning, salt, and black pepper. Stir and cook for 1 minute until fragrant.
Pour in beef broth and whole milk, then add the uncooked penne pasta. Stir to combine.
Bring the mixture to a boil, then reduce heat to medium-low. Cover and simmer for 12-15 minutes, stirring occasionally, until pasta is tender and most of the liquid is absorbed.
Remove the pot from heat and stir in unsalted butter and grated Parmesan cheese until melted and creamy.
Sprinkle chopped fresh parsley over the pasta and stir gently to combine.
Serve immediately while hot.