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Prep the Cake & Cherries: Trim any domed portions of the cooled cakes. Reserve trimmings and crumble to use as decoration later.
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Reserve 8 cherries for décor, if you like and pat them very dry with paper towels. Chop the rest of the cherries and set aside.
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Make the Chocolate Whipped Cream: Place the cream, confectioners’ sugar, cocoa and vanilla in a chilled mixing bowl and beat with an electric mixer just until soft peaks form. Take care at this point and just whip a tiny bit more until the cream is stiff but not over-whipped.
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Set aside about one-third of chocolate whipped cream in a small mixing bowl and fold in the chopped cherries to create the filling.
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Finish the Cake: Place one cake layer on your serving platter. Spread chocolate whipped cream filling over the top, stopping about ¼-inch (6 mm) from the edges. Place second cake layer on top and cover top and sides with most of the reserved chocolate whipped cream, smoothing with an offset spatula. Press some of the reserved cake crumbs along the bottom edge, as seen in image, if using.
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Insert star tip in pastry bag, add some chocolate whipped cream, and pipe rosettes as desired on top of cake. Sprinkle shaved chocolate in center of cake, if using. Cake may be refrigerated at this point up to overnight in a covered cake dome. Place reserved whole cherries, patted very dry, on rosettes right before serving.