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Add stout to a small pot, heat to just about boiling. Once you see a few bubbles start forming, turn the burner off and cover with lid.
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Remove the stems from the dried chiles and shake out the seeds into the garbage can.
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Add the chiles and raisins to the hot stout. Cover with lid and let sit for 20 minutes while you get the other ingredients together.
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Heat a cast iron skillet over medium/high heat for a few minutes. Remove skin from onion and garlic. Add the onion to the hot skillet and char on each side. Do the same with the garlic cloves. Garlic should be a deep golden color, not black or dark brown. Onion should look charred and almost black on each side.
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Reduce the heat to medium. Remove the charred garlic and onion. Set off to the side. Add the pumpkin seeds and cinnamon stick to the hot pan. Toast until the pumpkin seeds start to pop. Add to the same plate as the garlic and onion.
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Remove the stem/core from the tomato. Add the tomato to the same hot skillet. Char on each side, about 10 minutes. Remove and set off to the side. Once the tomato is cool enough, peel off as much skin as you can.
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Remove chiles and raisins from the soaking liquid and add to a blender along with 1 cup of the warm stout. Puree until smooth.
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Add the charred onion, garlic, pumpkin seeds, cinnamon stick, oregano, salt, pepper, and tomato to the blender. Puree until smooth.
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Place a fine mesh strainer inside a medium mixing bowl. Pour the sauce into the strainer a little at a time. Using the back of a spoon, work the sauce back and forth until only the solids remain. Continue process until all the sauce has been strained.
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Wash out the cast iron skillet you used before with a damp towel. Put it back on the burner over medium/low heat. Heat until hot again, about 5 minutes.
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Add the chocolate and stir until combined and melted. Add more salt and pepper based on your taste preferences.
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Let the sauce cool to room temperature then add to glass heatproof jar and store int he fridge for up to two weeks.