Heat the olive oil in a large Dutch oven over medium heat. Add the onion, carrots, celery, salt, and pepper. Sweat the veggies, stirring often, until softened but not browned, about 8-10 minutes.
Add the ground beef and break apart to fully cook.
Add the white wine and cook until very little liquid remains, another 8-10 minutes.
Reduce to a low heat before adding the pumpkin, milk, and remaining ingredients. Cover and simmer for 45-60 minutes (or longer) to allow flavors to develop. Salt and pepper to taste before serving. (I added about 1 tsp of additional salt.)
Serve with your choice of pasta, freshly grated parmesan or Pecorino Romano, and fresh parsley.