In a medium saucepan, combine 1 pound of fresh or frozen cherries, ¼ cup of granulated sugar, and half of the ¼ cup of amaretto. Simmer on medium heat for 5-7 minutes until the cherries soften and begin to release their juice. Remove from heat, let it cool, then stir in the remaining amaretto and 1 cup of cherry juice for a vibrant flavor.

In a large bowl, beat 1 ½ cups of heavy cream with ½ cup of powdered sugar using an electric mixer on medium speed until soft peaks form, about 3-5 minutes. In a separate bowl, mix 8 ounces of softened mascarpone cheese and 1 teaspoon of vanilla extract until smooth. Gently fold the whipped cream into the mascarpone mixture until fully combined.

Briefly dip 16 to 18 ladyfinger cookies in the cherry-amaretto mixture, ensuring a quick soak without oversaturating. Arrange the soaked ladyfingers in a single layer at the bottom of a 9x9-inch dish. Spread half of the mascarpone mixture over the ladyfingers, then add half of the cherry mixture, repeating the layers.

Cover the assembled Cherry Amaretto Tiramisu with plastic wrap and refrigerate for a minimum of 4 hours, preferably overnight.

Before serving, dust the top of the Cherry Amaretto Tiramisu with cocoa powder or grated dark chocolate. Garnish with fresh cherries or a sprig of mint.