Heat up olive oil in a shallow Dutch oven and add Italian sausage and hot pepper flakes. Remove the casing and break up the sausage with a wooden spoon.
Add more olive oil to the pot, chop garlic, and cook for a minute. Add broccoli rabe to the pot.
Add a ladle of pasta cooking water to the pot to wilt the broccoli rabe slowly and cover it until cooked.
Cook pasta in a pot of boiling salted water until al dente. Save some pasta cooking water before draining the pasta.
Add cooked pasta to the pot with sausage and broccoli rabe and stir to combine. Add more pasta cooking water to create a sauce that coats the pasta evenly.
