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Step 1
To make the chicken fried steak, cut the steak into 4 evenly sized pieces. Pound each piece with a meat tenderizer to about a 1/4-inch thickness and almost doubled in surface area. Lightly season the steaks with salt and pepper.
Step 2
For the breading, whisk together the flour, salt, pepper, cumin, oregano, and cayenne. Beat the egg and milk in a bowl wide enough to accommodate the steaks. Coat both sides of one piece of steak with the flour mixture, dip into the egg mixture, dredge in flour again, and place on a second large plate. Repeat with remaining steaks.
Step 3
Preheat the oven to 200°F and line a baking sheet with aluminum foil.
Step 4
In a large skillet over medium-high heat, warm 1 inch of oil to 300°F. Working in batches, gently place the steaks in the skillet in a single layer. There will be a lot of popping and hissing, so be careful. After 2 to 3 minutes, or when juices start bubbling out of the top of the steak, use tongs to gently flip the steaks and continue to cook until lightly browned, about 3 more minutes. Transfer the steaks to the prepared baking sheet and place in the oven to keep warm. Repeat with the remaining steaks.
Step 5
To make the chile gravy, reserve 1/4 cup of oil from the skillet, then drain the rest and wipe out the skillet with a paper towel. (If your oil is too burnt tasting, you can use fresh oil or bacon grease.) Return the oil to the skillet and warm over medium-low heat. Add the onion and while occasionally stirring, cook until softened, about 5 minutes. Add the garlic and cook for 30 more seconds.
Step 6
Whisk in the flour to the skillet until everything is well combined. Cook for a minute or until just beginning to brown, then stir in the broth, chili powder, cumin, oregano, and black pepper. While stirring, cook until the sauce has thickened, about 5 minutes. Stir in the jalapeño pickle juice then taste and adjust seasonings, adding salt if needed.
Step 7
Remove the steaks from the oven. Turn on the broiler, position a rack 6 inches from the heating element, and place each steak on an oven-proof plate. Evenly pour over the steaks the gravy, then top with the cheese. Slide the plates under the broiler (depending on the size of your oven, you may need to do this in batches), and cook until the cheese has melted, about 1-2 minutes. Garnish the steaks with pickled jalapeños. Serve immediately, with refried beans and rice, if you like.
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