n a small bowl, mix the cherries with the Amaretto and sugar. Let the mixture sit for 30 minutes, giving it a stir every so often.
In a large mixing bowl, blend the mascarpone cheese, powdered sugar, and vanilla extract until the mixture is smooth and creamy.
In a separate bowl, whip the heavy cream until it forms stiff peaks, then gently fold it into the mascarpone mixture until fully combined.
Quickly dip each ladyfinger into the cooled espresso and place a layer of them on the bottom of your serving dish.
Spread half of the mascarpone mixture evenly over the ladyfingers.
Spoon half of the cherry mixture on top of the mascarpone layer.
Repeat the process with another layer of espresso-dipped ladyfingers, the remaining mascarpone mixture, and the rest of the cherries.
Finish by dusting the top with cocoa powder and, if you like, garnish with shaved dark chocolate.
Chill in the refrigerator for at least 4 hours before serving to allow the flavors to meld.