Whip the cream. In a chilled bowl, combine heavy cream, powdered sugar, and vanilla. Whip until soft peaks form—light, airy, and perfect for layering.
Prep the coffee-cocoa mix. In a shallow dish, mix espresso (or coffee) with cocoa powder. This is your dipping magic for the cookies.
Dip the cookies. One at a time, quickly dunk each cookie into the coffee-cocoa mixture. Don’t soak—just a light coat.
Layer the cake. In a loaf pan or dish of choice, arrange a layer of dipped cookies. Spread a layer of whipped cream on top. Repeat until cookies and cream are gone, finishing with cream.
Chill it. Cover and refrigerate for at least 4 hours, ideally overnight. The cookies soften and absorb the mocha flavor, creating that dreamy icebox cake texture.
Add toppings. Right before serving, sprinkle with chocolate shavings, a dusting of cocoa, or a pinch of instant coffee for drama.