Preheat oven to 400 degrees F. Line a large baking sheet with parchment paper.
Roll out the puff pastry dough a bit. Cut each sheet into 9 squares.
Place 2 raspberries and 1 Rolo in the center of a square. Moisten the edges with a little water.
Bring two opposite corners of the square up to meet each other, and pinch down the sides to seal them together. Then pull all the corners up to the top (with the pouch of filling below) and pinch them together. Roll the pinched top down, and check that there are no gaps on the pouch. Place it on the prepared baking sheet. Repeat with remaining dough squares, raspberries and Rolos.
Brush the tops of the pastries with the half and half. Sprinkle the decorating sugar generously over the tops.
Bake the puffs for about 18 minutes until the tops have started turning golden brown. Remove them from the baking sheet to a serving plate.
They are best served while still warm, but allow the puffs to cool for 10 minutes before serving as the filling is quite hot after baking.