In a medium saucepan over medium heat, combine your pitted cherries, granulated sugar, and half of the amaretto liqueur. Stir gently for 5–7 minutes, until the cherries soften and start to release their juices. Once bubbling, remove from heat and let cool. Stir in the remaining amaretto and a splash of cherry juice for extra flavor before moving on to the next step.

In a large mixing bowl, whip the heavy cream and powdered sugar together until soft peaks form, using an electric mixer on medium speed, about 3–5 minutes. In another bowl, beat the mascarpone cheese with vanilla extract until smooth and creamy. Carefully fold the whipped cream into the mascarpone mixture until just combined.

Grab your ladyfinger cookies and briefly dip each one into the cherry-amaretto mixture, turning quickly to prevent them from getting too soggy. Aim for a quick dip of about 1-2 seconds.

In a 9x9-inch dish, start your assembly by arranging a single layer of soaked ladyfingers at the bottom. Spread half of the creamy mascarpone mixture over the ladyfingers, followed by half of the cherry mixture. Repeat the process with another layer of soaked ladyfingers, the remaining cream mixture, and the remaining cherry mixture.

Cover the assembled Cherry Amaretto Tiramisu with plastic wrap and refrigerate for at least 4 hours, though overnight is preferred.

When ready to serve, dust the top of your chilled Cherry Amaretto Tiramisu with cocoa powder or finely grated dark chocolate. Garnish with fresh cherries or mint leaves.