Preheat the oven to 400F. Coat a 9×13 baking dish with cooking spray.
Coat the bottom of the prepared baking dish with ½ cup enchilada sauce and spread it out evenly.
In a large bowl, toss together cooked/shredded chicken, pineapple tidbits, pineapple juice, ½ cup enchilada sauce, 2 cups shredded cheddar, garlic powder, cumin, salt and pepper then toss to mix and combine.
Layout one tortilla on a work surface, fill with ⅓ - ½ cup of filling mixture from the large bowl in step 3 then roll the tortilla up and place it seam side down in the prepared baking dish. Repeat with remaining tortillas and filling.
Top the dish with the remaining enchilada sauce and remaining shredded cheese then bake for 18-22 minutes or until the sauce is bubbling and the cheese is melted.
Serve enchiladas with desired toppings and enjoy!