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In a large soup pot or Dutch oven, cook the sausage over medium heat, breaking it up with a metal spatula, until it’s in small, bite-size pieces. Continue cooking until it’s nice and golden brown. Remove the sausage to a plate with a slotted spoon. Leave 2 tablespoons of fat in the pot and discard any extra.
Add the onion to the pot and cook over medium-low for 4-5 minutes, until softened and translucent. Stir the onions occasionally as they cook, scraping up the brown sausage bits on the bottom of the pan as the onions give off their juices.
Add the garlic and Italian seasoning. Cook for another 30 seconds, stirring continuously. Pour the wine into the pot and bring to a boil. Cook, stirring occasionally until most of the liquid has been evaporated.
Add the chicken broth, Italian sausage and lentils to the pot and bring to a boil.
While the mixture is coming to a boil, drain the roasted red peppers and discard the liquid. Break the peppers into bite-size pieces with your fingers and add to the pot. Next drain the tomatoes over a bowl, reserving the liquid. Break the tomatoes into bite-size pieces with your fingers and add to the pot along with the tomato liquid.
Add the bay leaves, salt and pepper to the pot and bring to a boil. Reduce to a nice steady simmer and cook, covered (with the lid slightly vented), for 45-50 minutes. Remove from heat and add the red wine vinegar and chopped basil. Stir to combine.
Taste the soup. The lentils should be firm, but creamy on the inside.(Black lentils can vary in their cooking time depending on their age, so you may need to cook some a bit longer.) Add more salt, if needed. Remove the bay leaves. I like to let this soup sit for about 30 minutes before serving to allow the flavors meld and marry. Serve garnished with more fresh basil and a bowl of shaved parmesan to pass at the table. Enjoy!