In a large bowl, beat mascarpone, powdered sugar, and vanilla extract until smooth, about 1–2 minutes.
In a separate chilled bowl, whip heavy cream to stiff peaks, about 2–3 minutes.
Gently fold whipped cream into mascarpone mixture until silky and combined.
Assembly
Stir amaretto and cherry juice in a shallow dish.
Quickly dip each ladyfinger into the mixture for 1–2 seconds to avoid sogginess.
Arrange half of the dipped ladyfingers in a 9×9-inch dish and spread half of the cream over them.
Scatter half of the cherries over the cream layer.
Repeat with remaining ladyfingers and cream.
Top with remaining cherries, dust with cocoa powder, cover, and refrigerate for at least 4 hours.
Before serving, add extra cherries or chocolate shavings if desired.
Notes
Testing Note: A brief rest after assembly preserves the ladyfingers’ slight bite.Cover tightly to prevent the cream from absorbing fridge odors.Store chilled up to 3 days at or below 40°F.