Preheat your oven to 400°F (200°C). Peel, seed, and cube the butternut squash if you haven't already. In a large bowl, toss the squash cubes with 1 tablespoon olive oil, salt, and black pepper to preference, making sure they're evenly coated. Spread the seasoned squash on a parchment paper-lined baking sheet in a single layer, being careful not to overcrowd. Roast in the preheated oven on the middle rack for about 30 minutes, or until fork-tender and lightly caramelized. Remove from the oven and set aside.
Meanwhile, trim the ends of the Brussels sprouts, remove any yellow leaves, and slice each sprout in half. In a medium bowl, toss the halved sprouts with 2 tablespoons olive oil, salt, and black pepper as needed. Spread them on a parchment paper-lined baking sheet in one layer without overcrowding. Roast on the middle rack at 400°F (you can do this at the same time as the squash) for 20-30 minutes, until golden and crisp-tender. Remove from the oven when done.
While the vegetables are roasting, bring a large pot of water to a boil. Add the cheese-filled tortellini and cook according to the package instructions, usually about 3-5 minutes. Drain the tortellini once it's cooked and set aside. I always stir the tortellini right after draining to prevent them from sticking together.
Slice the boneless, skinless chicken thighs into thin strips. Season the strips generously with smoked paprika, 1/4 teaspoon salt, and freshly cracked black pepper to taste. Heat a large cast-iron skillet over medium heat for about 3 minutes to ensure it's properly preheated. Add 2 tablespoons of olive oil, then arrange the chicken in a single layer without overcrowding—work in batches if necessary. Cook the chicken over medium heat for 4 minutes without moving so it gets a good sear. Flip the pieces, reduce the heat to low-medium, and cook another 5 minutes or until fully cooked through. Transfer the cooked chicken to a plate.
In the now-empty skillet used for the chicken, add 3 tablespoons butter and minced garlic. Cook over low-medium heat for 1-2 minutes, stirring frequently, until the garlic softens but doesn't brown. Add the drained, cooked tortellini from Step 3 and toss to thoroughly coat with the garlic butter. Then, return the cooked chicken from Step 4 to the skillet and stir well so everything is evenly coated. Remove the skillet from heat once everything is well-mixed. For a more aromatic touch, I sometimes add a little of the fresh thyme at this stage to infuse flavor into the sauce.
Add the roasted butternut squash from Step 1 and roasted Brussels sprouts from Step 2 into the skillet with the chicken and tortellini mixture. Gently toss everything together to combine, ensuring the vegetables remain intact. If your skillet isn't large enough, combine the ingredients in a large serving bowl. Top with fresh thyme and season with additional salt and freshly ground black pepper to taste before serving. I love how the fresh thyme brings all the flavors together right at the end.