Heat 1 tablespoon of olive oil in a large deep skillet over medium heat. Add the fresh sage leaves and fry for 1 to 2 minutes until dark green and crisp. Remove with a slotted spoon onto a paper towel; set aside for garnish.

In the same fragrant sage-infused oil, add the diced shallot and minced garlic. Sauté for 2 minutes until soft and aromatic without burning.

Add the cubed butternut squash, vegetable broth, sea salt, and black pepper to the skillet. Bring to a vigorous boil, then cover and simmer over medium-low heat for 12 to 14 minutes until the squash is completely fork-tender.

Transfer the tender squash and broth mixture into a high-speed blender (or use an immersion blender directly in the pot). Add the heavy cream, grated Parmigiano-Reggiano, and ground nutmeg. Blend on high speed for 60 seconds until completely silky, glossy, and velvety smooth.

Meanwhile, bring a large pot of salted water to a rolling boil. Cook penne pasta until 1 minute shy of al dente (about 9 minutes). Reserve 1 cup of starchy pasta water before draining.

Pour the velvety butternut squash sauce back into the skillet over low heat. Add the drained penne pasta and 1/4 cup of the reserved pasta cooking water. Toss and stir continuously for 2 minutes until the sauce coats every crevice of the penne in a rich, glossy emulsified sheen. Add more pasta water if a looser consistency is desired.

Ladle the steaming creamy pasta into warm shallow ceramic bowls. Crown each portion with the crispy fried sage leaves, delicate curls of shaved parmesan, toasted pepitas, and a crack of fresh black pepper. Serve immediately with warm crusty bread!