In a large bowl, whip heavy cream until soft peaks form. Add in mascarpone cheese, powdered sugar, and vanilla extract. Whip until smooth and fluffy.
In a shallow bowl, combine cooled espresso with amaretto liqueur. This mixture will help infuse each ladyfinger with rich coffee flavor.
Quickly dip each ladyfinger into the espresso mixture and line the bottom of a 9×9-inch dish with these dipped cookies.
Spread half of the whipped mascarpone cream mixture evenly over the ladyfingers.
Spoon half of the cherry preserves over the cream layer along with fresh cherry halves.
Repeat layering by adding another round of dipped ladyfingers followed by the remaining mascarpone cream and then topping it off with the rest of the cherry mixture.
Cover your dish tightly and refrigerate it for at least six hours—or better yet, overnight!
Dust the top generously with unsweetened cocoa powder and decorate with fresh cherries, shaved chocolate, or sliced almonds.
Slice into portions and serve chilled.