Place dried chiles in a large skillet over medium heat and toast until fragrant, about 2 minutes per side.
Place toasted chiles in a bowl of hot water and soak for 20 minutes until softened; drain and blend with 1 cup of beef stock until smooth.
Heat oil in a large Dutch oven over medium-high heat and sear beef cubes in batches until browned on all sides; remove beef and set aside.
In the same pot, sauté onion until translucent, approximately 5 minutes, then add garlic, cumin, oregano, and cayenne, cooking for 1 minute.
Return the beef and any accumulated juices to the pot, then stir in the chile paste and remaining beef stock.
Bring to a boil, then reduce heat to low, cover, and simmer for 150 to 180 minutes or until beef is fork-tender.
Whisk masa harina with 3 tablespoons of water to create a slurry and stir into the chili; simmer for an additional 10 minutes to thicken.
Season with salt and pepper to taste before serving.