Heat a large skillet over medium-high heat. Add dried chiles; cook, turning occasionally, until toasted and blistered in spots, 3 to 5 minutes. Add 1 cup water to just cover the chiles and bring to a simmer over medium-high. Cover and cook, undisturbed, until softened, about 5 minutes. Drain well.

Combine 2/3 cup onion, chipotle peppers, orange juice, vinegar, olive oil, achiote paste, garlic, cumin, brown sugar, and salt in a blender; process until marinade is smooth, about 30 seconds. Reserve 1/2 cup marinade, cover, and refrigerate until ready to use.

Place remaining marinade in a shallow dish or large resealable plastic bag. Add chicken; toss to coat evenly. Cover with plastic wrap; refrigerate for at least 8 hours or up to 24 hours.

Place wooden skewers in a shallow dish; cover with water by 1 inch. Let stand at room temperature while chicken marinates.

Preheat the oven to 400 degrees F (200 degrees C). Position an oven rack 8 inches away from the heating element. Line a small roasting pan or 9x13-inch baking dish with aluminum foil.

Thread 1 pineapple slice onto 2 skewers, being sure to pierce through the center core (skewers will be about 1 inch apart), leaving a 1 1/2-inch space from the end of the skewer. Thread 5 to 6 pieces of marinated chicken, stacking on top of pineapple; thread 1 pineapple slice. Repeat process, ending with pineapple slice, until all chicken pieces and pineapple slices are used, making 4 stacks total. Brush with any excess marinade in the bowl.

Place stacked skewers in the prepared pan, resting skewer ends on the edge of the pan so chicken doesn’t touch the bottom of the pan.

Bake in the preheated oven for 30 minutes. Flip skewers and brush with reserved 1/2 cup marinade. Continue baking until chicken is no longer pink in the center and the juices run clear, about 30 minutes more. An instant-read thermometer inserted into the center of meat should read 160 degrees F (71 degrees C). Turn on the oven’s broiler; broil until browned and crispy, 3 to 5 minutes. Flip and broil until browned and crispy on the other side, 3 to 5 minutes.

Meanwhile, heat a large skillet over high heat. Working two at a time, add tortillas; cook, turning once, until heated and browning in some spots, 1 to 2 minutes per side. Repeat with remaining tortillas.

Remove chicken and pineapple from skewers, place on a cutting board, and roughly chop.

Divide chicken and pineapple between heated tortillas; top with remaining 2/3 cup onion and cilantro. Recipe developed by Melissa Gray