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Step 1
Place dried peppers into a bowl or jar and fill with water until covered. Soak 1 to 4 hours until softened.
Step 2
Season chuck roast with salt and pepper. Heat a large cast iron pot over high heat. Add in 2 tablespoons olive oil. Sear chuck roast on all sides. Once seared, remove pot from heat and set aside.
Step 3
In a blender, add in guajillo peppers, ancho peppers, chipotle, garlic, cider vinegar, brown sugar, salt, oregano, cinnamon, remaining 2 tablespoons olive oil, and water. Blend until smooth, adding more water if necessary to thin it out enough to blend.
Step 4
Pour sauce over chuck roast in the pan. Place the lid on and braise in a 300 degree oven for 3 hours, until meat is tender and easily shreds with a fork.
Step 5
Shred and serve. Serving Suggestion: serve on a warmed corn tortilla with some red onion, cilantro, and jalapeno.