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

Add minced garlic and cook for an additional minute until fragrant.

Stir in crushed tomatoes, vegetable broth, sugar, dried basil, salt, and pepper. Bring to a simmer.

Reduce heat and let simmer for 20 minutes, stirring occasionally.

Stir in heavy cream and adjust seasoning if necessary. Keep warm on low heat.

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

Cut in cold butter until the mixture resembles coarse crumbs.

Stir in shredded cheddar cheese, buttermilk, garlic powder, and parsley until just combined.

Drop spoonfuls of the dumpling mixture onto a baking sheet lined with parchment paper.

Bake in a preheated oven at 400°F (200°C) for 15-20 minutes until golden brown.

Ladle the warm tomato soup into bowls and top with cheddar bay dumplings.

Garnish with additional parsley if desired and serve hot.