In a medium saucepan over medium heat, combine the cherries, granulated sugar, and half of the amaretto. Stir occasionally as the mixture simmers for 5-7 minutes, allowing the cherries to soften and release their juices. Once done, remove from heat, let cool slightly, then add the remaining amaretto and cherry juice, mixing well until combined.

In a large mixing bowl, beat the heavy cream with powdered sugar using an electric mixer on medium speed until soft peaks form. In a separate bowl, combine the mascarpone cheese with vanilla extract, mixing until smooth. Gently fold the whipped cream into the mascarpone mixture until well incorporated.

Take the ladyfinger cookies and briefly dip them into the cherry-amaretto mixture, ensuring they are soaked but not overly soggy. In a rectangular serving dish, layer the soaked ladyfingers, followed by half of the cream mixture and then half of the cherry filling. Repeat the process with the remaining ingredients, finishing with a layer of cream on top.

Cover the assembled tiramisu tightly with plastic wrap or a lid and refrigerate for at least 4 hours, but preferably overnight.

Once set, remove the tiramisu from the refrigerator. Just before serving, dust the top with cocoa powder or grated dark chocolate.