To start, toast some dried chiles in a Dutch oven. Simmer in beef stock for 10-15 minutes until the chiles soften.
Turn off the heat and pour the contents of the Dutch oven into a blender. Add the chipotle peppers and adobo sauce. Blend until smooth.
Season the chuck roast with salt and pepper and rub with flour. The flour helps create a crust. Cook the chuck roast in hot oil on both sides until a crust forms.
Remove the chuck roast and set it aside for now. Add the onion and jalapeños to the pot. Cook until softened, about four to five minutes. Add the garlic and cook for 30 seconds.
Pour in the dried Chile paste, beef stock, coffee, tomato paste, diced tomatoes and seasonings. Add the chuck roast.
Bring the chili to a boil. Place in a 275-degree F oven. Cook until the beef easily shreds with a fork, about three hours. Alternatively, you can simmer it on the stove until tender.
Remove chili from the oven and shred the meat. Stir in the beans. Mix some cornstarch with water and also stir that in to thicken.
Now add your favorite toppings and dig into the most delicious bowl of tender chuck roast chili! You'll love every spicy spoonful.
Oh my, this chili was absolutely delicious! That chile paste is everything. I've always used chili powder, but it made a huge improvement in flavor.