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Heat 1 tablespoon of olive oil in a large sauté pan with a lid. Add the sausage pieces and fry over medium-high heat for 10 minutes, stirring regularly, until they're golden-brown all over. Transfer the browned sausages to a plate, leaving any rendered fat in the pan.
Add the chopped onion and fennel to the hot pan and fry for 15 minutes, stirring occasionally, until they're soft and caramelized. If the pan starts to look dry, add another teaspoon or so of olive oil. Stir in the paprika, garlic, and half of the fennel seeds, frying for another 2 minutes until fragrant. Pour in the red wine and boil for 30 seconds, letting it reduce by half.
Add the chopped tomatoes, caster sugar, 100ml water, the seared sausage, and half a teaspoon of salt to the pan. Cover the pan and let it simmer for 30 minutes. After 10 minutes, remove the lid and continue cooking until the sauce has thickened significantly. The sauce should be rich and coat the back of a spoon.
Remove the pan from the heat, then stir in the pitted black olives and the remaining fennel seeds. Set the sauce aside while you prepare the pasta.
Combine all the pesto ingredients except the basil in the small bowl of a food processor. Add 1 tablespoon of water and blitz until you have a rough paste. Add the basil leaves and blitz again until everything is just combined. Be careful not to overblend the basil, as a lighter touch yields a better texture for the pesto.
Spoon a generous amount of the warm sausage ragù over each bowl of rigatoni, then top with a spoonful of the fresh pesto. If you have any, finish with a sprinkling of chopped fennel fronds for a bit of extra freshness, and serve immediately.
Per serving
Allergen information is derived automatically from the ingredient list and is a guide, not a guarantee. Always check the packaging of the products you cook with.
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