Combine the 8 chicken thighs, 1 oz ranch seasoning, lime juice, 7 oz pickled jalapeno juice, and 2 tbsp of the olive oil in a bowl, stirring well to coat all the chicken evenly. Cover and refrigerate for at least 2-3 hours—this allows the flavors to penetrate the meat and keeps the chicken moist during cooking. While the chicken marinates, you can prepare the other components.

While the chicken marinates, make the ranch dressing by whisking together the mayonnaise, sour cream, half and half, 0.4 oz ranch seasoning, dried onion, worcestershire sauce, horseradish, and 3 tbsp pickled jalapenos until smooth. Refrigerate until ready to use. Separately, cook the bacon strips until crispy, then crumble them into roughly 1/2-inch pieces and set aside. I like to have all these components ready before cooking because the quesadilla assembly happens quickly once the chicken is done.

Heat a griddle or large skillet to 400-450°F. Remove the marinated chicken from the refrigerator and carefully place the thighs on the hot griddle. Cook for 3-5 minutes per side until the internal temperature reaches 165-170°F when checked with a meat thermometer. The high heat will create a flavorful crust while the marinade keeps the inside juicy. Let the cooked chicken rest for 5-10 minutes, then dice it into bite-sized pieces.

Reduce the griddle temperature to 375-400°F. Lay out all 5 flour tortillas on a clean surface. Spread a thin layer of softened cream cheese on each tortilla, then divide the shredded cheddar and colby jack cheeses evenly across all tortillas, spreading them in an even layer. This creates a foundation that helps bind everything together and ensures every bite has melted cheese.

Add the remaining 2 tbsp olive oil to the griddle and place the cheese-covered tortillas on it, cooking for 3-4 minutes until the bottom becomes golden and the cheese begins to melt. While the bottoms cook, divide the diced chicken from Step 3, crumbled bacon from Step 2, and 3 tbsp diced pickled jalapenos between the tortillas, arranging them on one half of each tortilla. Drizzle generously with the cracked chicken sauce from Step 2.

Once the bottom is golden and the cheese is melted, fold each tortilla in half over the filling using a spatula. Continue cooking for another 2-3 minutes, gently pressing down to help the cheese seal, until both sides are toasted golden brown and the cheese is completely melted throughout. I find that folding halfway through cooking helps the cheese melt evenly while creating crispy exterior texture on both sides.

Transfer the finished quesadillas to a cutting board and let them cool for 4-5 minutes—this brief rest allows the cheese to set slightly, making them easier to cut and preventing the filling from spilling out. Cut each quesadilla in half or into triangles with a sharp knife, then serve immediately with extra cracked chicken sauce on the side for dipping.