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Gently fold 1 cup of whipped cream into the cooled vanilla pudding. If desired, transfer remaining whipped cream to a piping bag fitted with a star tip. This can be used for decorating the top of the trifle.
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Slice strawberries into rounds. Set aside.
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Combine the rum and sherry in a small bowl. Set aside.
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Using a small spaulta, spread a layer of red raspberry preserves on the bottom of each trifle dish (ex: wine glass, small bowl, etc).
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Use a small round cookie cutter to cut the cakes into rounds that will fit into your chosen trifle dish.
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Place 1 cake round into the bottom of the dish, crust side up. Using a pastry brush, brush some of the rum and sherry mixture onto the top of the cake.
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Spoon some of the pudding mixture onto the cake and press in a few of the strawberry rounds.
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Repeat this process so that you have 3 cake layers.
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If desired, pipe whipped cream on the top layer and decorate with fresh strawberries.
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Once assembled, place in the refrigerator to chill for 8 hours before serving.