Begin by placing 8 fresh pineapple rings in a medium bowl. Pour in the dark rum and coconut rum, ensuring they are fully submerged. Let the pineapple rings soak for at least 1 hour, allowing the flavors to infuse.

Pat the rings dry gently with paper towels and reserve the remaining rum for the dipping sauce.

Set up your workstation with three separate bowls. In the first bowl, add all-purpose flour; in the second, whisk together large eggs and coconut milk until well combined. Finally, place sweetened coconut flakes in the third bowl.

Take one soaked pineapple ring and dip it into the flour, ensuring it's fully coated. Then transfer it to the egg mixture, allowing any excess to drip off. Finally, roll the ring in the coconut flakes, pressing gently to ensure the flakes stick well.

Heat vegetable oil in a deep frying pan to about 350°F (175°C). Carefully place the coated pineapple rings in the hot oil, ensuring they are not overcrowded. Fry for roughly 1 minute per side, or until golden brown and crispy.

Use a slotted spoon to remove them, draining on paper towels to absorb any excess oil.

In a medium bowl, combine softened cream cheese and powdered sugar, mixing until smooth. Gradually stir in the reserved rum from the pineapple soak to reach your desired dipping sauce consistency.