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Step 1: Prepare ingredients by bringing a large pot of water to a boil over high heat. Rinse all produce, pat spinach dry with paper towel, halve tomatoes, peel onion, halve, and thinly slice. Step 2: Cook chicken by patting chicken dry with paper towel and seasoning all over with 1/2 teaspoon salt and pepper as desired. Heat 1/2 tablespoon olive oil in a large pan over medium-high heat. When oil is shimmering, add chicken and sear, working in batches and adding oil as needed, until cooked through and no longer pink, about 6 minutes per side. Transfer chicken to cutting board and set aside to rest, reserving the pan for Step 4. Step 3: Cook penne by seasoning boiling water generously with salt. Stir in penne and cook until al dente, about 6 minutes. Reserve 3/8 cup of pasta cooking water, then drain and set aside. Step 4: Caramelize onion by placing the pan from chicken over medium heat and adding butter and onion. Cook, stirring, until onion is soft and translucent, 5–6 minutes. Add white wine and continue cooking, scraping up browned bits from bottom of the pan, until liquid is reduced by half, 2–3 minutes more. Meanwhile, cut rested chicken into 1/4-inch slices. Step 5: Season penne by adding 1/6 cup heavy cream and cooked penne to the pan with onion, still over medium heat, and stirring to combine. Add 1/4 cup reserved pasta cooking water and stir to coat noodles with sauce, 1–2 minutes more. Remove the pan from heat, saving the remaining cream for another use. Step 6: Plate pesto chicken penne by adding pesto, spinach, tomatoes, and sliced chicken to the pan with penne. Stir vigorously to fully coat with pesto, adding more pasta water, 1/2 tablespoon at a time, as needed. Taste and add salt and pepper as desired, then divide among serving bowls. Garnish with Parmesan and roughly tear basil leaves over top, discarding stems.
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