Preparation

1. Preheat oven to 325F. Season beef all over with salt and pepper; set aside and let sit for at least 45 minutes before cooking.
2. In a large Dutch oven, heat olive oil over medium-high heat until shimmering. Add carrots, celery, and about ⅓ of the onions. Season with a pinch of salt and cook until softened but not browned, about 5 minutes.
3. Add tomato paste and about 1/4 cup wine and mix in with the carrots, onion, and celery. Season to taste with salt, then place another ⅓ of the onions in an even layer on top of the cooked vegetables. Reduce heat to medium-low and add beef, nestling pieces into onion mixture in a single layer. Cover the beef with remaining onions, add italian seasoning and season lightly with salt. Cover pot with lid and transfer to oven.
4. Cook, checking and stirring about every hour, until onions are very soft and have melted into the sauce and the beef is fall apart tender. About 2.5-3 hours.
5. Using tongs, remove beef set aside to cool slightly. Return dutch oven to stovetop over medium heat until sauce is simmering. Add remaining 3/4 cup wine and cherry tomatoes to onion mixture and bring to a simmer over medium-low heat. Once beef is cool enough to handle, cut into 1 1/2-inch pieces and add back to the pot. Season with salt to taste and cook, stirring occasionally, until tomatoes burst and mixture is reduced to a saucy, thickened consistency, about 15 minutes. Beef should begin to shred into the sauce but still with some larger chunks remaining.
6. Meanwhile, in a pot of salted boiling water, cook pasta until just shy of al dente according to directions on the package. Reserve at least 1 cup of pasta water, then drain and transfer pasta to the sauce.
7. Increase heat to high and cook, stirring rapidly, until pasta is al dente and sauce is thickened and coats noodles, 1 to 2 minutes, adding more pasta water in 1/4 cup at a time as needed. Season with salt to taste. Divide into bowls and top with grated parmesan.