Prep the Chicken Pockets: Place chicken breasts flat on a cutting board. Insert a sharp knife horizontally into the thickest part of each breast, cutting deep to create a pocket without slicing completely through to the other side.

Season the Exterior: Drizzle the outside of the chicken breasts with 1 tablespoon of olive oil. Rub the paprika, garlic powder, dried oregano, salt, and black pepper evenly over all sides of the chicken.

Make the Filling: In a medium bowl, thoroughly combine the chopped baby spinach, crumbled feta, chopped Kalamata olives, drained sun-dried tomatoes, and minced garlic.

Stuff and Close: Divide the filling equally into three portions and stuff them generously into the chicken pockets. Press the edges closed and secure tightly with 2-3 toothpicks per breast.

Sear to Golden Brown: Heat a splash of olive oil in a large skillet over medium-high heat. Add the chicken and sear undisturbed for 5 minutes on each side until a deep golden-brown crust forms.

Simmer with Tomatoes: Scatter the halved cherry tomatoes into the skillet around the chicken. Reduce heat to medium-low, cover with a tight-fitting lid, and simmer for 10-12 minutes until the chicken reaches an internal temperature of 165°F (74°C).

Garnish and Serve: Remove from heat, carefully extract the toothpicks, garnish with chopped fresh parsley, and spoon the warm pan juices over the top before serving.