In a large pot over medium heat, warm olive oil until shimmering. Add chopped onion and sauté for about 5 minutes until the onion becomes translucent.

Toss in minced garlic, cooking for another minute until aromatic.

Stir in chopped ripe tomatoes, vegetable broth, sugar, salt, and black pepper. Bring to a boil, then reduce to low and simmer for 20 minutes.

Use an immersion blender to blend the soup until velvety smooth. Stir in heavy cream and chopped basil.

In a mixing bowl, whisk together flour, baking powder, garlic powder, and salt.

Cut cold butter into the flour mixture using a pastry cutter until it resembles coarse crumbs.

Gently fold in shredded cheddar cheese, milk, and parsley until just combined.

Drop spoonfuls of dumpling dough into the simmering soup. Cover and cook undisturbed for 10-12 minutes.

Remove the lid and allow dumplings to cook for an additional 2 minutes.

Ladle the warm soup into bowls, ensuring each serving includes dumplings.