Combine cooled espresso and amaretto in a shallow bowl. Set aside.
Beat cold heavy cream to soft peaks. Set aside.
Beat mascarpone, powdered sugar, amaretto, and vanilla until smooth. Gently fold in whipped cream in two additions.
Dip ladyfingers 1 to 2 seconds per side and layer across the bottom of the dish.
Spread half the mascarpone cream, then the cherry filling, then a second layer of dipped ladyfingers.
Top with remaining cream. Cover and refrigerate at least 6 hours or overnight.
Dust with cocoa powder just before serving. Garnish with fresh cherries if desired.