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Prep Time: 50 minutes
Preheat the oven to 400 degrees. Place the squash on a baking sheet, cut side up, and rub with a 1/2 Tbsp. of olive oil. Season with a pinch of salt and place into the oven until completely tender and slightly browned, about 30 minutes. Meanwhile, in a large sauté pan or soup pot over low flame, heat the bacon until the fat starts to render, stirring occasionally. While the bacon is rendering, bring a large pot of salted water to a boil over a high flame for the pasta. Continue cooking the bacon until browned, crisp, and all fat is rendered, about 20 minutes. Remove the bacon to a plate lined with paper towels, reserving 1 Tbsp. bacon fat in the pan. Return the pan to the low flame and add the leeks with a pinch of salt. Stir frequently, "melting" the leeks, about 15 minutes.
When the squash is cooked, scoop the flesh out with a large spoon into a blender or food processor. Blend with 1 Tbsp. olive oil and a pinch of salt and pepper until smooth. Add the pasta to the boiling water and cook until al dente, about 5 minutes, reserving 1/2 cup of the pasta water. Return the pasta to the pot along with the water and the squash puree. Stir gently to combine.Add the bacon to the leeks and stir to combine. Divide the pasta between 2 plates and top evenly with the bacon and leek mixture. Garnish with dabs of capri and a pinch of pepper.