Preheat oven to 180°C.
Sprinkle pineapple with cracked pepper. Place the butter and sugar in a small saucepan over low heat, stirring until sugar has dissolved, then cook for a further 1-2 minutes. Pour into the base of 4 x 10cm ovenproof pie dishes. Place a pineapple ring, peppered-side down on top of the mixture.
Roll out pastry to 5mm thick and cut out 4 x 12.5cm circles. Prick with a fork. Top each dish with a circle of pastry, pressing to the edges to seal. Bake for 25 minutes until pastry is puffed and golden. Allow to sit for 5 minutes before turning out. Serve with ice-cream, if desired.