Cooking Steps

1. 

   Prepare ingredients

   Preheat oven to 450ºF. Rinse all produce. Pick cilantro leaves, discarding stems. Halve grape tomatoes. Mince garlic. Halve poblano lengthwise; using a knife tip, discard seeds and stem, then cut into ¼-inch dice (be sure to wash your knife, cutting board, and hands afterward).

2. 

   Sear steaks

   Pat steaks dry with paper towel and season all over with ½ teaspoon salt and pepper as desired. Heat ½ tablespoon olive oil in a medium pan over medium-high heat. When oil is shimmering, add steaks and sear until browned and medium rare, 4-6 minutes per side. Transfer steaks to a plate and set aside to rest, about 5 minutes. Wipe pan clean and reserve, off heat, for Step 5.

3. 

   Make chimichurri

   While steaks sear, in a blender or food processor, combine red wine vinegar, Cholula (skip or use half for less heat), cilantro, garlic, 3 tablespoons olive oil, ¼ teaspoon salt, and pepper as desired. Blend until smooth. Alternatively, finely chop cilantro and combine in a bowl with remaining chimichurri ingredients. Set aside. In a small bowl, combine Cheddar and Monterey Jack.

4. 

   Assemble and bake quesadillas

   Once rested, cut steaks against the grain into ¼-inch slices. Rub a baking sheet with 2 teaspoons olive oil, then add 2 tortillas, side by side. Layer with half of cheeses, then add steak and 1 teaspoon chimichurri. Top with remaining cheeses and remaining tortillas. Brush tops of quesadillas with 1 teaspoon olive oil each, then bake until golden and crisp, 5-7 minutes.

5. 

   Make poblano salsa

   While quesadillas bake, return pan from steaks to medium-high heat with 2 teaspoons olive oil. When oil is shimmering, add poblano and sauté, stirring, until soft, about 5 minutes. Add grape tomatoes and season with ½ teaspoon salt and pepper as desired. Cook, stirring, until vegetables are very soft, about 3 minutes more. Remove pan from heat.

6. 

   Plate steak quesadillas

   Using a thin spatula, carefully loosen steak quesadillas from baking sheet, transfer to cutting board, and cut into quarters. Transfer to serving plates and top with poblano salsa. Drizzle over a spoonful of chimichurri. Serve remaining chimichurri alongside for dipping. Enjoy!