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Step 1
Preheat your oven to 350°F.
Step 2
Heat the 2 tablespoons oil in a deep sauté pan. Add chiles and fry for 30 seconds each. Remove and place on paper towels to drain.
Step 3
When the chiles are slightly cooled, place them in your blender. With the blender running, slowly pour in the oil used for frying in a steady stream. Add the brown sugar, chocolate, and salt (about ¼ teaspoon). The mixture should be fairly coarse.
Step 4
In a small bowl, stir together the garlic, shallots, salt (about ½ teaspoon), pepper, and just enough olive oil to barely cover meat. Rub the mixture over skirt steak.
Step 5
In a heavy skillet or saucepan over high heat, sear or grill the skirt steak for 10 minutes, turning frequently. Let cool.
Step 6
Cover the steak with the chile mixture.
Step 7
Place the steak in oven and finish cooking for 5 to 7 minutes.
Step 8
Remove the steak from the oven, and let it rest for 10 minutes. Slice and serve with fresh, seasonal vegetables and tortillas.