2tablespoonsfresh oreganochopped; or 1 tablespoon dried
For the Filling:
2tablespoonsvegetable oil
2large onionschopped
4 to 5garlic clovesminced
4(7 ounce) candiced green chiles
2teaspoonsdried oregano
2teaspoonsground cumin
2teaspoonschili powder
2tablespoonsbutter
2tablespoonsall-purpose flour
1cupreserved beef liquid from the beef roast
12Tortillas
16ouncesMonterey jack cheeseshredded
2tablespoonsolive oil
Instructions
Braise the Beef
Preheat the oven to 275°F. Season both sides of the chuck roast with salt and pepper.
Heat 1 to 2 tablespoons vegetable oil in a large oven-safe pot over medium heat. Sear the roast for 2–3 minutes per side until browned. Transfer to a plate.
Pour the red wine into the pot and scrape up the browned bits from the bottom. Return the roast to the pot.
Add enough beef stock to come halfway up the meat. Stir in bay leaves and oregano. Cover with a lid and braise in the oven for 6–7 hours, or until the beef shreds easily with a fork.
Remove the roast from the pot and reserve 1 cup of the cooking liquid. Shred the beef while still warm and place it in a large bowl.
Make the Filling
Heat 2 tablespoons vegetable oil in a large skillet over medium heat. Add onions and cook until softened, about 5 minutes. Stir in the garlic and cook 1 minute more.
Remove from heat, add green chiles, dried oregano, cumin, and chili powder. Transfer this mixture to the bowl of shredded beef.
In the same skillet, melt butter over medium heat. Whisk in flour and cook for 2 minutes.
Slowly whisk in the reserved 1 cup beef cooking liquid. Cook until smooth and slightly thickened, 2–3 minutes.
Let the sauce cool slightly, then pour over the beef mixture. Stir until well combined.
Assemble the Chimichangas
Preheat the oven to 425°F. Line a baking sheet with parchment paper and lightly coat with nonstick spray.
Working with one tortilla at a time, spoon about ¾ cup beef filling into the center. Add 2–3 tablespoons shredded Monterey Jack (reserve remaining cheese for topping).
Fold the left and right sides in toward the center, then roll tightly from the bottom up. Place seam-side down on the baking sheet. Repeat with remaining tortillas and filling.
Bake and Serve
Brush the tops of the chimichangas with olive oil. Bake for 15–20 minutes, or until golden and crisp.
Sprinkle remaining cheese over the chimichangas and bake 2 minutes more, until melted.
Brown the beef first: Searing the chuck roast before braising develops a richer, deeper flavor in the finished filling.
Deglaze for flavor: Adding wine to the hot pot after browning loosens the flavorful browned bits from the bottom. If you prefer not to use wine, substitute an equal amount of beef broth.
Slow-cooker option: You can cook the chuck roast in a slow cooker on Low for 8–10 hours, adding the wine (or broth), stock, herbs, and seasonings as directed.
Cheese swaps: Monterey Jack gives a mild, creamy flavor, but Cheddar or Pepper Jack can be used.
Make ahead: The shredded beef mixture can be prepared up to 3 days in advance and stored in the refrigerator, or frozen for up to 2 months.
Freezer-friendly chimichangas: Assemble and freeze before baking. Bake from frozen at 375°F for 25–30 minutes, adding extra time as needed until hot and crisp.