Preheat your oven to 425°F.
In a saucepan over medium-low heat, melt the butter. Add shallots and garlic, stirring occasionally, and cook until softened and slightly golden, about 5-6 minutes. Stir in the tomato paste and let it cook for 3-4 more minutes.
Add the tomatoes, sherry, chicken stock, brown sugar, basil, salt, and pepper, and bring everything to a low boil. Reduce the heat to a simmer, allowing the flavors to blend for about 20 minutes.
Carefully transfer the soup to a blender and puree until smooth, then pour it back into the pot over low heat. Stir in the heavy cream and seasonings. Taste and adjust seasoning with additional salt and pepper as needed.
Set 4-5 ramekins on a baking sheet. Using one of the ramekins as a guide, cut 4-5 squares from the puff pastry sheet. Ladle the soup into the ramekins, filling each.
(I forgot to video this step, but don't skip it - it's divine!!) Sprinkle ¼ cup of grated cheese over each ramekin of soup, then place a puff pastry round on top. Brush the pastry with egg wash and sprinkle with an additional 1-2 tablespoons of cheese.
Bake for 20-25 minutes or until the puff pastry is golden, puffed, and fully cooked.