Blend the chipotles and all their adobo sauce with the avocado oil, annatto, coriander, cumin, garlic powder, oregano, salt, pineapple juice, lime juice, vinegar, and cilantro. Stop when the mixture looks uniformly reddish-orange, without visible chile pieces.

Coat the thighs thoroughly with the blended mixture in a large zipper bag or bowl, then refrigerate for at least 2 hours and no more than 10 hours. Turn the meat through the sauce so it reaches the folds as well as the broad surfaces.

Heat the grill to approximately 400°F using medium-high heat. The cooking surface should be hot enough to produce a steady sizzle when the chicken lands.

Trim away the pineapple's crown, base, and peel, then cut the fruit into rounds 1 inch thick. Keep the slices intact for easier handling on the grates.

Transfer the thighs to the grill with tongs, leaving excess used marinade behind, and cook for 5–6 minutes on each side; grill the pineapple for 3–5 minutes per side. Look for dark char spots on the chicken and browned patches on the fruit, but use a meat thermometer to check chicken doneness rather than relying on color or timing alone.

Move the fully cooked chicken onto a clean cutting board and give it a 5-minute rest. The pause lets the meat settle before cutting, with glossy juices still visible beneath the browned coating.

Cut the rested thighs and grilled pineapple into slices or bite-size dice. A similar piece size makes the chicken and fruit easier to combine evenly.