Prepare the Cherry Amaretto Layer

1. Cook the Cherries: In a small saucepan, combine the cherries, amaretto, and sugar (if using). Cook over medium heat for about 5 minutes, stirring occasionally, until the cherries have softened and released some of their juices. Remove from heat and let cool.
2. Set Aside: Once cooled, set the cherry mixture aside while you prepare the other layers. This allows the cherries to marinate in the amaretto for maximum flavor.

Prepare the Mascarpone Layer

1. Whip the Cream: In a large mixing bowl, beat the heavy cream with powdered sugar and vanilla extract until stiff peaks form. You can use a hand mixer or a stand mixer for this step.
2. Combine Mascarpone: In a separate bowl, whisk together the mascarpone and amaretto liqueur until smooth.
3. Fold the Mixtures Together: Gently fold the whipped cream into the mascarpone mixture. Be careful not to deflate the whipped cream too much – you want to keep it light and airy.

Prepare the Ladyfingers

1. Soak the Ladyfingers: In a shallow dish, combine the espresso and amaretto liqueur. Quickly dip each ladyfinger into the mixture, making sure not to soak them for too long (about 1 second per side). The goal is to moisten them without making them soggy.
2. Layer the Ladyfingers: Arrange the soaked ladyfingers in a single layer at the bottom of a 9×9-inch serving dish or a similar-sized dish.

Assemble the Tiramisu

1. First Layer: Spread half of the mascarpone mixture evenly over the ladyfingers.
2. Add Cherries: Spoon half of the cherry and amaretto mixture on top of the mascarpone layer.
3. Repeat Layers: Dip the remaining ladyfingers in the espresso-amaretto mixture and arrange them over the cherry layer. Top with the rest of the mascarpone mixture and the remaining cherries.
4. Chill: Cover the dish with plastic wrap and refrigerate for at least 4 hours, or preferably overnight, to allow the flavors to meld and the tiramisu to firm up.

Serve and Garnish

1. Dust with Cocoa Powder: Just before serving, dust the top of the tiramisu with cocoa powder. You can use a fine-mesh sieve to achieve an even dusting.
2. Optional Garnish: For extra decadence, sprinkle some shaved dark chocolate on top of the tiramisu for a chocolatey finish.