Preheat your oven to 400°F (200°C) and line a baking sheet with parchment paper for easy cleanup.
Toss the pumpkin cubes with 2 tablespoons olive oil, a generous pinch of salt and pepper on the prepared baking sheet. Spread them out in a single layer, ensuring they’re not overcrowded.
Roast the pumpkin for 25-30 minutes until the edges are caramelized and the flesh is tender when pierced with a fork. The caramelization adds incredible flavor depth.
While the pumpkin roasts, heat the remaining olive oil in a large pot over medium heat. Add the diced onion and cook for 5-7 minutes until translucent and beginning to soften.
Add the minced garlic and diced red pepper to the pot and cook for another 2-3 minutes until fragrant and softened.
Stir in the smoked paprika, cumin, and cayenne pepper and cook for 30 seconds until aromatic, being careful not to burn the spices.
Add the roasted pumpkin to the pot along with the vegetable broth and bay leaf. Bring the mixture to a simmer.
Reduce heat and simmer for 15 minutes to allow the flavors to meld together.
Remove the bay leaf and blend the soup until completely smooth using an immersion blender or working in batches with a regular blender (be careful with the hot liquid).
Return the soup to the pot if needed, stir in the sherry vinegar, and adjust seasoning with salt and pepper to taste.
Serve hot with your choice of garnishes – a drizzle of good olive oil and toasted pumpkin seeds add wonderful texture contrast.