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Prepare the spicy marinade: In a medium bowl, combine the chipotle peppers, adobo sauce, minced garlic, minced serrano pepper, orange juice, lime juice, 1 tablespoon of olive oil, ground cumin, dried oregano, salt, and black pepper. Whisk vigorously until well combined. For a smoother marinade, you may blend all ingredients in a small food processor until puréed.
Marinate the steak: Place the trimmed flank steak in a large zip-top bag or a shallow non-reactive dish. Pour the prepared marinade over the steak, ensuring it is thoroughly coated. Seal the bag or cover the dish and refrigerate for at least 30 minutes, and up to 2 hours, to allow the flavors to meld. For best spicy flavor, marinate for at least 1 hour.
Preheat the oven: While the steak is marinating, preheat your oven to 400°F.
Sear the steak: Remove the steak from the marinade, allowing any excess marinade to drip off (discard the used marinade). Heat 1 tablespoon of olive oil in a large oven-safe skillet (cast iron or stainless steel recommended) over medium-high heat. Once the oil is shimmering, carefully place the steak in the hot skillet. Sear on all sides until a deep golden-brown crust forms, about 2 to 3 minutes per side, for a total of 6 to 9 minutes depending on thickness.
Roast the steak: Transfer the skillet with the seared steak to the preheated oven. Roast for 5 to 10 minutes, or until an instant-read thermometer inserted into the thickest part of the steak registers an internal temperature of 130°F for medium-rare, or 135-140°F for medium.
Rest and slice: Carefully remove the skillet from the oven. Transfer the cooked steak to a clean cutting board. Tent loosely with aluminum foil and let it rest for 5 to 7 minutes. This resting period is crucial for the juices to redistribute, ensuring a tender and moist result. After resting, slice the steak thinly against the grain and serve immediately.

Prepare the spicy marinade: In a medium bowl, combine the chipotle peppers, adobo sauce, minced garlic, minced serrano pepper, orange juice, lime juice, 1 tablespoon of olive oil, ground cumin, dried oregano, salt, and black pepper. Whisk vigorously until well combined. For a smoother marinade, you may blend all ingredients in a small food processor until puréed.
Marinate the steak: Place the trimmed flank steak in a large zip-top bag or a shallow non-reactive dish. Pour the prepared marinade over the steak, ensuring it is thoroughly coated. Seal the bag or cover the dish and refrigerate for at least 30 minutes, and up to 2 hours, to allow the flavors to meld. For best spicy flavor, marinate for at least 1 hour.
Preheat the oven: While the steak is marinating, preheat your oven to 400°F.
Sear the steak: Remove the steak from the marinade, allowing any excess marinade to drip off (discard the used marinade). Heat 1 tablespoon of olive oil in a large oven-safe skillet (cast iron or stainless steel recommended) over medium-high heat. Once the oil is shimmering, carefully place the steak in the hot skillet. Sear on all sides until a deep golden-brown crust forms, about 2 to 3 minutes per side, for a total of 6 to 9 minutes depending on thickness.
Roast the steak: Transfer the skillet with the seared steak to the preheated oven. Roast for 5 to 10 minutes, or until an instant-read thermometer inserted into the thickest part of the steak registers an internal temperature of 130°F for medium-rare, or 135-140°F for medium.
Rest and slice: Carefully remove the skillet from the oven. Transfer the cooked steak to a clean cutting board. Tent loosely with aluminum foil and let it rest for 5 to 7 minutes. This resting period is crucial for the juices to redistribute, ensuring a tender and moist result. After resting, slice the steak thinly against the grain and serve immediately.