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 another minute until fragrant.

Stir in crushed tomatoes, vegetable broth, sugar, basil, oregano, salt, and pepper. Bring to a simmer and cook for 20 minutes.

Remove from heat and stir in heavy cream. Blend the soup until smooth using an immersion blender or in batches with a regular blender.

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

Fold in shredded cheddar cheese.

In another bowl, mix milk and melted butter. Pour into the dry ingredients and stir until just combined.

Drop spoonfuls of the dumpling mixture onto the simmering soup. Cover and cook for 10 minutes until dumplings are cooked through.

Ladle the soup into bowls and top with the cheddar bay dumplings. Enjoy hot!