Prepare the Coffee
Brew the coffee according to package directions.
Set aside 2 tablespoons of the brewed coffee.
Pour the remaining coffee into a shallow bowl for dipping the cookies.
Make the Mascarpone Filling
In a medium bowl, combine the softened mascarpone cheese, maple syrup, and vanilla extract.
Stir until smooth and creamy.
Add the Greek yogurt and mix until fully incorporated.
Spoon or pipe approximately ¼ cup of the mixture into the bottom of each serving glass.
Add the First Cookie Layer
Break 2 Biscoff cookies into 3 pieces each.
Quickly dip the cookie pieces into the coffee, ensuring they are coated but not overly soaked.
Layer the dipped cookies over the mascarpone mixture in each glass.
Prepare the Cookie Butter Drizzle
Place the reserved 2 tablespoons of coffee in a microwave-safe bowl.
Heat until hot.
Stir in the Biscoff cookie butter until smooth.
Drizzle 1–2 teaspoons over the cookie layer in each glass.
Build the Layers
Add another layer of dipped Biscoff cookies.
Spoon another layer of mascarpone-yogurt filling over the cookies.
Repeat with another layer of dipped cookies.
Drizzle with more cookie butter mixture.
Finish with a final layer of dipped cookies.
Top with whipped cream if desired.
Finish and Chill
In a small bowl, combine the cocoa powder and espresso powder.
Use a fine-mesh sieve to dust the mixture over the tops of the dessert cups.
Cover each glass with plastic wrap.
Refrigerate for at least 1 hour before serving.