Season shrimp with a little salt and pepper.
In a large pot, deep skillet or dutch oven add 1 tablespoon of the olive oil over low-medium heat.
Once warm add shrimp and cook for about 3-4 minutes stirring occasionally.
Remove shrimp to a plate or bowl lined with a paper towel.
Add second tablespoon olive oil to pot and heat.
Add garlic and ½ the red pepper flakes. Sauté for a few minutes.
Pour in crushed tomatoes, diced tomatoes and a can full (32 oz) of water. Turn heat to high.
Once arrabbiata sauce begins to boil, stir in salt, pepper and remaining red pepper flakes. *See note in post on controlling how spicy this dish is.
Cover, turn down heat to low and simmer for about 15 minutes. Stir occasionally. After 15 minutes taste test. Add more salt, pepper or red pepper flakes if you wish.
Meanwhile bring a salted pot of water to boil and cook squid ink pasta according to package directions.
Once cooked drain squid ink pasta. Add pasta directly to arrabbiata sauce. Toss to combine.
Add Parmesan and fresh basil. Stir to combine.
Add in shrimp and toss to combine once more.
Serve with additional Parmesan and fresh basil on top if desired.