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For the soup:
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Preheat your oven to 400 F.
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In a baking dish or on a rimmed sheet pan, place the chicken breasts, drizzle with olive oil and season with salt and pepper. Roast chicken in the oven for 30 minutes. Remove it from the oven and set aside to cool. Shred chicken and set aside for later use.
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On a sheet pan place the cut tomatoes, cherry tomatoes and garlic cloves. Give them a big drizzle of olive oil and a big season of salt and pepper. Roast in the oven for 15 minutes. Remove pan from the oven and set aside to cool. Remove the garlic cloves from the skins by squeezing them out into the dish. Set aside for later use.
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In a large Dutch oven or pot add the 2 tablespoons of olive oil and 2 tablespoons of butter. Heat over medium high heat. Add the onion and carrot. Sweat veggies until onions are translucent and carrots are tender, about 8 minutes. Add the tomato paste and stir until combined and mixture is thick. You can almost start smelling the tomato paste cook and that's what gives you the clue it's time to de-glaze the pot with the wine. Add the wine and stir it in until mixture looks saucy. Reduce for 2 minutes. Add the can of diced tomatoes and Italian seasoning. Stir in and cook for another 2 minutes.
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Add the roasted garlic cloves and the whole sheet pan of roasted tomatoes to the pot.
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Let the whole mixture in the pot come to a boil then reduce the heat and simmer everything for 15 minutes.
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So at this point I used an immersion blender, however, a food processor or blender works just as good. Blend the whole mixture together, add a little bit of chicken stock to the mixture if needed to help blend. Blend until mixture is smooth.
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Add the chicken stock into the pot with the pureed vegetable mixture and increase heat to bring the soup to a boil. Reduce heat and simmer soup for another 15 minutes. Stir frequently to prevent from burning on the bottom of the pot.
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Season with the teaspoon of salt and pepper. Add the shredded chicken and turn heat down to low while you prepare the dumplings.
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For the dumplings:
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In a medium size bowl add the polenta, flour, baking powder, garlic salt, Parmesan, parsley, garlic and basil.
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In a separate bowl whisk together the egg, milk and olive oil.
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Create a well in the center of the dry ingredients and pour the wet ingredients in the center. Start by folding the wet ingredients into the dry ingredients until mixture is completely combined and looks crumbly.
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The dough should mold together easily. Pack 2 tablespoons of mixture into tight balls. Use an extra dusting of flour if it's too sticky. The mixture should make about 9-10 even-sized dumpling balls. If the dumplings aren't packed tightly enough they will fall apart when cooking.
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Bring a large pot of salted water to a boil. Using a slotted spoon, slowly drop each ball into the boiling water. Once they rise to the surface, cook for 10 minutes until they are tender.
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I tried a tester dumpling first just to be sure my cooking time was right. Everyone's stove is different so account for your burners idiosyncrasies. I definitely had to adjust my cooking time accordingly. The dumplings should be slightly puffed up and tender.
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When done, remove dumplings from the water with a slotted spoon to a plate. Remove soup from the heat and add the dumplings right on top.
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Serve big ladle fulls into a bowl or plate and garnish with basil, grated Parmesan and and a side of garlic bread. Enjoy!
