Preheat the oven to 350˚. Heat the olive oil in a large Dutch oven over medium heat until it shimmers. Add the chopped onion, carrots, celery and a pinch of salt and cook, stirring occasionally, until soft, 10 to 12 minutes. (Alternatively, you can work in a non-ovenproof pot and transfer your mixture to a baking dish when it’s time to move it to the oven.)
Add the cayenne, a few turns of pepper and the garlic to the pot and cook another minute, until fragrant. Add the wine and cook until it’s reduced by half, 3 to 4 minutes. Add the squash, tomatoes, broth, chickpeas, rosemary and bay leaves; give everything a stir.
Cover the pot, transfer to the oven and braise until the chickpeas are soft and the squash is tender, about 2 hours. Discard the bay leaves and rosemary sprigs before serving. Top with parsley, serve with bread and enjoy!