While the oven preheats and the water comes to a boil, start the sauce.
Add a small drizzle of olive oil to a cast iron skillet and bring to medium high heat. Add the prosciutto and saute, stirring frequently until crispy. Once crispy, use a slotted spoon to remove the prosciutto to a paper towel lined plate.
Add the cherry tomatoes to the pan, along with one or two tablespoons of olive oil. You want them to be evenly coated but not greasy. Season with salt and pepper.
Cook the cherry tomatoes over medium-high heat, stirring occasionally, until they are starting to pop and burst, 5 to 10 minutes. You want to see them develop some blistering.
Once the cherry tomatoes have started to pop, add the garlic and reduce heat to medium. Using a wooden spoon, break up the tomatoes. Keep the tomatoes and garlic moving in the pan so that the garlic doesn't burn, about 5 minutes.
Add the cream and basil. If 2 cups of heavy whipping cream is too fat/rich, you can use a mix of cream and reserved pasta cooking water. Bring to a boil, reduce heat and simmer another 5 to 10 minutes. Taste the sauce, then season with salt and pepper.
Optional: Stir in parmesan cheese right before serving.