Step 1: Preheat oven to 425°F.
Step 2: Mix coriander (refer to Note # 1 below), cumin, and cayenne in a small bowl. Sprinkle chicken with spice mixture, pressing to adhere; season with salt and pepper.
Step 3: Heat oil in a large ovenproof skillet over medium-high. Cook chicken, skin side down, until browned and beginning to crisp, about 5-8 minutes.
Step 4: Transfer chicken to a plate and arrange pineapple slices in the pan. *(NOTE: if you don't have an oven proof skillet, make sure you scrape every piece of the the brown bits from your skillet over the pineapple slices that have been placed into an oven-proof pan).*
Step 5: Place chicken, skin side up, on top of pineapple.
Step 6: Transfer to oven and roast until an instant-read thermometer inserted into the thickest part of thigh registers 165°F, 40–45 minutes.
Step 7: Meanwhile, bring chile, garlic, pineapple juice, vinegar, brown sugar, and paprika to a boil in a small saucepan and cook until thickened and syrupy, 12–15 minutes; season glaze with salt.
Step 8: When chicken is done, brush with glaze and roast just until glaze is bubbling, about 2 minutes (Refer to Note # 2); repeat with any remaining glaze. Transfer chicken and pineapple to a cutting board; let rest 10 minutes. Serve chicken and pineapple with any juices from skillet alongside.
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