Preheat the oven to 400°F.
Cut the honeynut squash in half, remove the seeds, and place it face-down on a parchment lined baking sheet.
Cut the top off of the garlic head and drizzle with a bit of olive oil. Wrap tightly in foil and add it to the baking sheet.
Roast the squash and the garlic for 30 minutes at 400°F or until the squash is very soft.
While the squash is roasting, thinly slice the onion and the brussel sprouts, then roughly chop the thyme and rosemary. Keep all of these separate and set them aside.
When the squash is out of the oven, scoop it add it to a blender with the vegetable stock. Squeeze in the garlic cloves. Blend until a smooth "honeynut broth" forms. Set this aside.
Put a large pot or sauté pan on medium heat. Add 1 tablespoon of olive oil to the pan and add in half of the brussel sprouts. Cook, stirring occasionally, until the brussel sprouts are starting to slightly charr on the edges, about 3-4 minutes. Remove from the pan and set aside for plating.
Add another glug of olive oil to the pan and add in the onions. Stir to coat them in the oil and cook for 4-5 minutes until softened. Add in the rosemary and thyme, season with salt and pepper to taste and stir.
If you are choosing to use it, add in the white wine and continue to cook for 2-3 minutes or until the alcohol has cooked off. This adds a gentle acidity to the soup that is just delicious, but totally optional.
Add in the Calabrian chili paste and stir to coat everything in it. Add in the butter beans and stir, cooking another 1-2 minutes.
Pour in the honeynut broth and stir to combine, let everything come to a gentle simmer.
When the broth is simmering, add in the remaining uncooked brussel sprouts. Cover and let the soup simmer an additional 15 minutes. *I choose to add the brussel sprouts at this step so that they maintain some color and texture, even as they cook through. It makes such a difference! Season the soup with salt and pepper as needed, and add a dash of red wine vinegar right before removing it from the heat.
To serve, generously portion into 4 bowls, top with the charred brussel sprout shred and eat with either crusty bread or warm rice.