Preheat your oven to 400°F. Place the diced butternut squash on a sheet pan, drizzle with 1/2 tablespoon of olive oil, and toss to coat. Roast for 20 minutes then add the kale to the sheet pan, toss together, and roast for 10 minutes, until the squash is tender and the kale is slightly crispy.

Heat the remaining 2 tablespoons of olive oil in a large skillet over medium heat. Add the diced onion and sauté for about 5 minutes, until translucent. Add the minced garlic and cook for another 2 minutes. Add the cherry tomatoes (whole) and sauté for about 5 minutes. Then, cover the skillet and let the tomatoes cook until they soften and begin to blister (about 5-10 minutes).

Transfer the cooked tomato mixture to a blender or food processor with the silken tofu, tomato paste, salt, black pepper, and red pepper flakes. Blend until smooth and creamy (about 1 minute). Add more salt and pepper to taste, if needed.

Bring a large pot of salted water to a boil. Cook the pasta according to the package instructions until al dente. Drain and return it to the pot.

Add the blended tomato-tofu sauce to the cooked pasta, stirring to coat evenly. Let it simmer for 1-2 minutes to allow the flavors to meld.

Fold in the roasted butternut squash and kale, and gently toss everything together.

Serve the pasta warm, garnished with freshly grated cheese and fresh basil.