Begin by placing your fresh pineapple rings in a large bowl. Pour the dark and coconut rums over the pineapple, ensuring each ring is well submerged. Cover the bowl and let the pineapple soak for at least 1 hour.

While the pineapple is soaking, set up your breading station with three shallow bowls. In the first bowl, add all-purpose flour for the initial coating. In the second, whisk together eggs and coconut milk. Finally, place sweetened coconut flakes in the third bowl.

Take each pineapple ring, dip it into the flour, then into the egg and coconut milk mixture, and finally roll in coconut flakes. Ensure each ring is fully coated.

Heat vegetable oil to 350°F (175°C) over medium heat. Carefully lower in the coated pineapple rings in batches and fry for about 1 minute on each side until golden brown.

Prepare the dipping sauce by combining softened cream cheese and powdered sugar in a mixing bowl. Gradually add the reserved rum from the soaking process and mix until smooth.