2-3 hours before cooking, wash your octopus thoroughly and pat dry with a paper towel. Place it in a serving or baking dish with a lid. Coat the octopus with oil and wine. Scatter sliced garlic cloves and peppercorns over it. Cover and let it marinate in the fridge for a couple of hours. It can also be prepared a day before and marinate overnight.
Transfer the octopus in a pressure cooker. If any bits and pieces of garlic and peppercorn are sticking on, don’t worry. Add water, just enough to cover it. I don’t use salt in this step because fresh octopus is already salty (and you will be salting the sauce and pasta water later). Seal the cooker and boil on medium heat for 17-20 minutes. You can use a regular pot and simmer for as long as you need to achieve preferred tenderness. It may take a bit longer, and you may also need to add more water.
Use tongs to remove the octopus from the pot onto a cutting board. Since it will be piping hot, the tongs will also help you handle it while cutting it into bite-sized pieces. Set aside.
Before making the sauce, make sure to strain the leftover water from the pot into a clean bowl (use a fine sieve). You will use it to boil the macaroni later.
Warm the olive oil in a large saucepan and add the crushed garlic. Stir to release its aroma, but only for a couple of seconds. Add the tomato puree, 150 ml warm water, season with salt and pepper to taste.
Add the octopus and simmer until the sauce thickens. It shouldn’t take more than 5-7 minutes.
Use this time to cook the pasta. Fill up a pot with water, and don’t forget to add the strained octopus’ water. Cook macaroni according to package directions.
Strain pasta, return to pot, add octopus with sauce, parsley, and mix well to combine.
Serve with freshly ground pepper and extra parsley on top.