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Preheat the oven to 350 degree F.
In a large, deep skillet (I prefer my 12-inch Lodge cast iron skillet) over medium high heat, cook and crumble the Italian sausage and oregano until no pink remains; drain any fats that accumulate.
Over medium heat, add the cream cheese chunks to the cooked sausage, gently stirring to allow the cream cheese to melt. Once the cream cheese is fully incorporated, slowly stir in the marinara sauce until well combined. Add the milk to the empty jar of marinara and shake well; add to the meat mixture.
Gently fold in the cooked tortellini; sprinkle the shredded cheese over the top.
Bake the tortellini, uncovered, for 10-15 minutes or until hot and bubbly throughout. Let rest 10 minutes before serving. Serve with grated Parmesan cheese, as desired.