Remove the core from the pineapple and brown slices in a hot frying pan for 1.5 minutes per side.
Flame rum in the pan, then add sugar and water and cook until a thickened caramel forms.
Season the sauce with black pepper and set aside.
Heat raisins and rum in a saucepan, then let soak for 15 minutes.
Whisk egg yolks and sugar together in a bowl.
Boil milk, pour over the egg mixture while whisking, and return to the saucepan.
Stir in cream, rum, and raisins, then cook over low heat until thickened without boiling.
Churn the cooled custard in an ice cream machine.
Bake thin pineapple slices on a tray at 180°C for 20 minutes.
Turn off the oven and let slices dry for 1.5 hours, turning once.
Layer cooked pineapple, top with ice cream and dried pineapple, then drizzle with sauce.