In a medium bowl, combine halved ripe cherries, sugar, and 2 tablespoons of amaretto. Stir gently and let the mixture sit for about 15 minutes, allowing the cherries to macerate.

Brew a strong cup of coffee and allow it to cool to room temperature. Add the remaining amaretto, stirring until well combined.

In a large mixing bowl, whip the heavy cream until stiff peaks form, about 3-5 minutes.

In a separate medium bowl, combine the mascarpone cheese, powdered sugar, and vanilla extract. Mix until smooth and creamy.

Gently fold the whipped cream into the mascarpone mixture using a spatula.

Quickly dip each ladyfinger into the coffee-amaretto mixture, ensuring they are moistened but not soggy.

In a rectangular dish, layer the bottom with the dipped ladyfingers. Spread half of the mascarpone mixture evenly over them.

Spoon half of the macerated cherries over the cream, spreading them out evenly.

Repeat the process with another set of dipped ladyfingers, followed by the remaining mascarpone mixture and cherries.

Cover the assembled tiramisu with plastic wrap and refrigerate for at least 4 hours.

Before serving, dust the top with cocoa powder and optionally garnish with extra cherries.