In a medium saucepan over medium heat, combine halved fresh cherries, granulated sugar, lemon juice, and Amaretto. Simmer for about 5–7 minutes until cherries soften. Cool completely.

In a large mixing bowl, pour in the cold heavy cream and beat until soft peaks form (3–5 minutes). In another bowl, blend mascarpone, powdered sugar, and vanilla until smooth. Fold whipped cream into mascarpone until combined.

Mix cooled espresso with remaining Amaretto in a shallow dish. Ensure it's cooled to prevent ladyfingers from becoming soggy while preparing layers.

Quickly dip ladyfingers into the espresso-Amaretto mixture. Arrange in an 8×8-inch dish in a single layer. Spread half of the mascarpone cream over ladyfingers, followed by half of the cherry mixture. Repeat layers.

Cover tightly with plastic wrap and refrigerate for at least 4 hours, preferably overnight, to allow flavors to meld and layers to firm up.

Before serving, dust with cocoa powder. Garnish with shaved chocolate and fresh cherries if desired.