Heat a medium pot over low to medium heat. Add ½ Tablespoon olive oil to lightly coat the bottom of the pan. Once hot, add the sun-dried tomatoes, garlic and sage. Stir for 1 minute until fragrant. Add the pumpkin puree, chicken broth, basil, and cinnamon to the pot, and stir well to combine. Bring to a low simmer for 15 minutes, stirring occasionally. After 15 minutes, remove from heat to let cool.
Meanwhile, heat a large pot over medium heat. Add the ground meat and brown completely. When completely brown, drain into a colander to remove any excess liquid.
Add ½-1 Tablespoon olive oil to the same large pot. Once hot, add the onions, carrots, and celery. Cook until vegetables are soft and translucent, 8-10 minutes stirring occasionally. When vegetables are soft, add the ground meat back to the pan and stir to incorporate into the vegetables.
Add the white wine to the pot to deglaze, scraping any brown bits off the bottom of the pan. Cook for 2 minutes to let the alcohol evaporate. After 2 minutes add the crushed tomatoes to the pot and stir well.
Once the pumpkin puree broth has cooled, add to a high speed blender. Blend until smooth. Add to the pot with the meat vegetable mixture and stir well to combine.
Add the milk to the pot and season with black pepper, stir well. Bring the sauce to a low simmer. Simmer for ~30 minutes-1 hour until thickened to your liking, stirring occasionally. If it becomes too thick add more broth. *See notes below
When ready to serve, bring a large pot of water to a boil. Add the pasta and cook according to the package instructions. Drain the pasta, top with sauce and garnish with parmesan cheese.