In a medium saucepan over low heat, combine 2 cups of pitted and halved fresh cherries, 3 tablespoons of granulated sugar, 1 tablespoon of lemon juice, and ¼ cup of Amaretto. Stir gently and cook for 5–7 minutes until the cherries soften and the mixture becomes syrupy. Remove from heat and let cool completely.

In a large mixing bowl, beat 1 cup of cold heavy cream using an electric mixer until soft peaks form, about 3–4 minutes. In another bowl, whisk together 1 cup of room-temperature mascarpone cheese, ⅓ cup of powdered sugar, and 1 teaspoon of vanilla extract until smooth and combined. Fold the whipped cream into the mascarpone mixture gently until light and fluffy.

In a shallow dish, mix together 2 tablespoons of Amaretto with ¾ cup of cooled brewed espresso. Allow the flavors to meld.

Dip each ladyfinger into the espresso-Amaretto mixture for 1–2 seconds per side to soak without getting too soggy. Layer soaked ladyfingers, mascarpone cream, and cherry mixture in a medium-sized dish. Repeat layers, finishing with a layer of mascarpone cream on top.

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

Before serving, dust the top with unsweetened cocoa powder and garnish with fresh cherries and shaved dark chocolate.