Add the crushed tomatoes, vegetable broth, dried basil, and dried oregano. Season with salt and pepper. Bring the mixture to a simmer and let it cook for 15 minutes, stirring occasionally.
Stir in the heavy cream and shredded cheddar cheese until melted and smooth. Remove from heat and set aside.
For the dumplings, in a mixing bowl, combine the flour, baking powder, garlic powder, dried parsley, and salt. Cut in the cold butter using a pastry cutter or your fingers until the mixture resembles coarse crumbs.
Stir in the milk and shredded cheddar cheese until just combined. Do not overmix.
Drop spoonfuls of the dumpling mixture onto the surface of the simmering soup. Cover the pot and let the dumplings steam for 15 minutes without lifting the lid.
Once the dumplings are cooked through, serve the soup hot, garnished with additional cheddar cheese if desired.
Notes
For a spicier kick, add a pinch of red pepper flakes to the soup while it simmers.
Substitute half of the heavy cream with Greek yogurt for a lighter version without sacrificing creaminess.