In a mixing bowl, blend the jerk seasoning, olive oil, salt, and pepper to create a flavorful marinade. Generously rub this mixture over the chicken thighs, ensuring they are evenly coated. Cover the bowl with plastic wrap and refrigerate for at least 1 hour, or overnight for a deeper flavor infusion.

While the chicken is marinating, preheat your oven to 400°F (200°C). Prepare a baking dish by lightly greasing it with olive oil.

In a medium saucepan over medium heat, combine the diced fresh pineapple, pineapple juice, honey, soy sauce, grated ginger, minced garlic, and lime juice. Stir until it begins to simmer, about 5-7 minutes.

Arrange the chicken thighs in the greased baking dish with the skin side up. Pour half of the prepared pineapple sauce evenly over the chicken. Bake for 25 minutes.

Cover the baking dish with aluminum foil to keep the chicken moist during the initial baking phase. After 25 minutes, carefully remove the foil.

Brush the chicken thighs with the remaining pineapple sauce, then return them to the oven without the foil. Bake for an additional 15-20 minutes until the chicken reaches an internal temperature of 165°F (74°C) and the skin is golden and crisp.

Remove from the oven and allow the chicken to rest for about 5 minutes to let the juices redistribute.

Sprinkle chopped cilantro over the chicken for an extra layer of flavor. Slice and serve with the remaining pineapple sauce, paired with rice, coleslaw, or a fresh salad.