Food Recipes Dinner Meat Dishes Smoky Pasilla-and-Citrus Grilled Flank Steak 5.0 (1) 2 Reviews On a recent trip to Oaxaca, I was mesmerized with the fruity, smoky pasilla de Oaxaca chiles so much that I brought back a bag of the chiles, as well as a basalt molcajete, in my suitcase. The deep flavor the chiles impart to beef is exceptional; if you can’t find them, chipotle morita or chipotle meco chiles are good substitutes. By Andrea Slonecker Updated on August 2, 2023 Tested by Food & Wine Test Kitchen Tested by Food & Wine Test Kitchen Recipes published by Food & Wine are rigorously tested by the culinary professionals at the Dotdash Meredith Food Studios in order to empower home cooks to enjoy being in the kitchen and preparing meals they will love. Our expert culinary team tests and retests each recipe using equipment and ingredients found in home kitchens to ensure that every recipe is delicious and works for cooks at home every single time. Meet the Food & Wine Test Kitchen Save Rate PRINT Share Close Photo: Photo by Victor Protasio / Food Styling by Margaret Dickey / Prop Styling by Heather Chadduck Hillegas Active Time: 40 mins Total Time: 1 hr Yield: 4 to 6 Cook Mode (Keep screen awake) Ingredients 6 medium-size dried pasilla de Oaxaca chiles (see Note) 1 tablespoon cumin seeds, toasted 1 teaspoon black peppercorns 5 garlic cloves 4 teaspoons kosher salt, divided 3/4 cup fresh orange juice (from 3 oranges) 1/4 cup fresh lime juice (from 2 limes) 1 (2-pound) flank steak Cilantro sprigs (leaves and thin stems) Warm corn tortillas, sliced radishes, and lime wedges, for serving Directions Heat a cast-iron skillet over medium-high, and add chiles. Press flat with the back of a spatula, and toast until slightly softened and a shade darker but not black, 10 to 15 seconds per side. Remove chiles from skillet, and let cool slightly. Wearing gloves if possible, trim stems; cut chiles open, and remove and discard seeds. Cut chiles into very small pieces. Place chile pieces in a small bowl, and add boiling water to cover. Let soak until soft and rehydrated, 10 to 15 minutes. Pour through a fine wire-mesh strainer into a bowl; discard liquid. Using a molcajete, pound and grind cumin seeds and peppercorns to a fine powder, about 3 minutes. Add garlic; pound and grind to a thick paste, about 1 minute. Add half of the rehydrated chiles and 1 teaspoon salt, and pound until not much of the chiles are visible, about 4 minutes. Add 1 teaspoon salt and remaining rehydrated chiles, and pound until mixture is a thick, relatively smooth paste, about 4 minutes. Add orange juice and lime juice, a little at a time, stirring with pestle to combine. Taste and adjust seasonings if needed. Season both sides of flank steak with remaining 2 teaspoons salt, and place in a shallow dish. Pour 1/2 cup chile sauce over steak, coating evenly. Set remaining chile sauce aside. Cover flank steak, and let stand at room temperature at least 2 hours or up to 4 hours. (Alternatively, marinate in refrigerator 8 hours. Let steak come to room temperature at least 1 hour before grilling.) Preheat grill to high (450°F to 500°F). Without brushing off marinade, place steak on oiled grates, and grill, uncovered, until charred and a thermometer inserted into thickest portion registers 125°F, 4 to 6 minutes per side. Remove steak from grill, cover with aluminum foil, and let rest 8 to 10 minutes (internal temperature will continue to rise). Cut steak against the grain into thin strips, and arrange on a serving platter. Serve steak with tortillas, remaining chile sauce, radishes, cilantro, and lime wedges. Make Ahead Chile paste can be prepared up to 3 days ahead and stored in an airtight container in refrigerator. Notes Dried pasilla de Oaxaca chiles may be ordered online. Suggested Pairing Earthy, malty beer. Originally appeared: May 2020 Rate It Print