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Pre-heat the oven to 180°C/350F/gas mark 4.
Cut the skin off the butternut squash and cut into medium-sized cubes. Place on a baking tray with the garlic cloves (skin still on). Sprinkle over the oregano, red pepper flakes, paprika and a pinch of salt and pepper.
Add the olive oil and rub over the squash with your hands so the squash and garlic are evenly coated in the spices. Roast in the oven for around 30 minutes until the squash and garlic are soft, toss halfway through.
After 20 minutes of roasting the squash bring a large pot of salted water to the boil. Add the penne and cook according to instructions until al dente, drain. Tip: Reserve 1-2 cups of pasta water before draining, see notes.
Once the squash is cooked, place in a food processor. Squeeze the garlic out of their skins and add that to the squash with the cream and parmesan. Blitz until smooth and creamy. Add extra salt if required.
Add the sauce to the drained pot you cooked the pasta in or a clean skillet and add 1 cup pasta water, stir to combine to thin out the sauce. If it's still too thick add more until you reach the desired consistency.
Add the cooked penne and toss until evenly coated in the sauce. Serve with torn basil leaves.