Preheat the oven to 250 degrees F. Prep a sheet pan with parchment paper. Pop popcorn in the microwave and pour into a large bowl.
Over medium-low heat, slowly melt caramels in a small pan with a splash of water. Stir frequently. Once melted, pour over the popcorn and toss until covered.
Lay flat on the baking sheet and bake for 20 minutes stirring halfway through. Once the popcorn has finished in the oven, let cool for about 30 minutes.
Melt the butter in a small pan and stir in the coconut. Stir often and be careful not to burn. Cook until lightly browned. Chop Samoas cookies into small pieces and set aside.
Melt the chocolate chips in the microwave. Start with 30 seconds, stir, and continue microwaving for 15 second increments until melted, stirring each time.
Drizzle chocolate over the cooled popcorn. Top with toasted coconut and Samoas pieces while the chocolate is still warm. Enjoy fresh!