In a medium saucepan over medium heat, combine pitted cherries and a splash of water. Mash slightly and boil for about 5 minutes. Strain into a bowl, mixing in lemon juice and sugar until dissolved. Cool completely.

In a large mixing bowl, whip heavy cream on high speed until stiff peaks form, about 3-4 minutes. In another bowl, whisk mascarpone, sugar, and vanilla until smooth. Gently fold in whipped cream and some cherry juice until combined.

Prepare a shallow dish with brewed coffee and cherry amaretto. Quickly dip each ladyfinger into the mixture for about 10 seconds. Arrange half in a layer at the bottom of your serving dish.

Spread half of the mascarpone filling over the ladyfingers, smoothing it with a spatula. Repeat layering with remaining ladyfingers and filling. Cover with plastic wrap and refrigerate for at least 6 hours, preferably overnight.

In another saucepan, combine frozen cherries, water, and sugar over medium heat. Cook for 7-10 minutes until the sauce thickens. Blend mixture until smooth and stir in optional amaretto and lemon juice. Cool completely.

Once set, remove from refrigerator. Drizzle cooled cherry sauce over top, garnish with fresh cherries and chocolate flakes, slice, and serve.