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Step 1
Preheat oven to 400°F. Using a large knife, split the two squash in half lengthwise. Use a spoon to remove the seeds and pulp. Place cut side down on a foil lined baking sheet and add 1 cup of water. Brush the outside of the squash with 1 tablespoon of olive oil. Bake for 30 to 40 minutes, or until the point of a small knife can easily pierce the skin.
Step 2
Chop the chicken breasts into bite-sized pieces and season with Italian seasonings, salt, garlic powder and black pepper. Heat the remaining 2 tablespoons of olive oil in a skillet over medium-high heat. Sauté the chicken chunks until golden and cooked through, about 7 to 8 minutes. The chicken is done when it feels firm to the touch and a meat thermometer inserted in the center reaches 170°F.
Step 3
When the squash is done, use two forks to rake the flesh of each to create “spaghetti.” Transfer into a large bowl and reserve the emptied skins. Toss the spaghetti squash with the pesto, mixing to coat the strands well. Add the cooked chicken and cherry tomatoes, and toss to combine.
Step 4
Portion the Chicken Pesto Squash back into the squash skin “bowls.” Sprinkle the top of each bowl with toasted pine nuts and serve.