In a large pot, heat olive oil over medium heat. Add chopped onion and sauté for about 5 minutes until translucent. Mix in minced garlic and cook for an additional minute.

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

Use an immersion blender to puree the soup until smooth. Stir in heavy cream and fresh basil, keeping warm over low heat.

In a separate bowl, whisk together all-purpose flour, baking powder, garlic powder, and salt.

Cut cold butter into the flour mixture until resembling coarse crumbs. Fold in cheddar cheese.

Stir in milk and parsley until just combined, forming a soft dough. Be careful not to overmix.

Drop spoonfuls of the dumpling dough into simmering soup, cover, and cook for 10 to 12 minutes.

After cooking, remove the lid and let dumplings cook for an additional 2 minutes.

Ladle the soup into bowls, serve immediately, and enjoy.