In a medium saucepan over medium heat, combine fresh cherries, sugar, lemon juice, and Amaretto. Cook for 5–7 minutes until the cherries soften and the mixture becomes syrupy. Stir occasionally to prevent sticking and allow the flavors to meld. Once done, remove from heat and let it cool completely.

In a large mixing bowl, whip cold heavy cream until soft peaks form, using an electric mixer on medium speed for about 2–3 minutes. In another bowl, mix mascarpone with powdered sugar and vanilla extract until the mixture is smooth and creamy. Gently fold the whipped cream into the mascarpone mixture using a spatula until well combined.

Brew a fresh cup of espresso and allow it to cool slightly. In a shallow dish, stir in a splash of Amaretto to the cooled espresso, enhancing the coffee flavor. This will serve as the soaking mixture for your ladyfingers.

Quickly dip ladyfingers into the espresso-Amaretto mixture for no more than 1–2 seconds, ensuring they absorb flavor without getting too soggy. Layer the dipped ladyfingers in an 8x8-inch dish, then spread half of the mascarpone cream over the top, followed by half of the cherry mixture. Repeat the layering with the remaining ingredients.

Cover your assembled Cherry Amaretto Tiramisu and place it in the refrigerator to chill for at least 4 hours, although overnight is preferred.

Once thoroughly chilled, dust the top generously with cocoa powder and shaved chocolate. For an extra burst of freshness, garnish with a few extra cherries. Slice into squares, serve, and enjoy!