Heat the olive oil in a large pot over medium-high heat. Add in the garlic and shallot and saute until fragrant, about 1 minute. Crumble the sausage into the pot and brown all over, but don’t cook through.
Pour in the vodka and cook until it slightly reduces, about 2 minutes. Add in the chicken stock and crushed tomatoes and bring to a low boil. Add in the penne and cook, stirring often, until pasta is al dente, about 15-20 minutes.
Reduce heat to low and add in the heavy cream, crushed red pepper flakes, dried oregano, salt, pepper, and basil leaves. Cook for 5 more minutes, or until warmed through, stirring occasionally. If your sauce becomes too thick, add a bit more chicken stock or water to thin.
Top with additional basil leaves and parmesan cheese, to serve.