Prepare the Cream Filling (5 minutes): In a medium mixing bowl, combine the Greek yogurt, maple syrup (or honey), and vanilla extract. Whisk vigorously for 60 seconds until the mixture is uniform, glossy, and light. The yogurt should go from thick and chunky to smooth and airy—you'll see tiny bubbles form on the surface. Taste it. If your yogurt is exceptionally tart, add an extra splash of maple syrup or honey and whisk again. Checkpoint: Your cream should taste balanced—not overly sweet, not sour.

Set Up Your Workspace (2 minutes): Pour your cooled espresso (it must be completely cold—room temperature is perfect) into a wide, shallow dish like a small plate or bowl. This makes it easy to dip the cookies quickly. Set out two small glasses or clear dessert cups side by side where you'll be working. Having everything in place keeps the assembly fast and prevents the cookies from falling apart before they land in the cup.

Build Layer 1—The Base (3 minutes): Take 1.5 to 2 ladyfingers and snap them in half gently so they fit inside your cup with a little overhang. Pick up one piece and dip it into the espresso for exactly 1 second on each side—count it out: "one-Mississippi, one-Mississippi." The cookie should feel slightly dampened but not soaked or soggy. Lay it immediately into the bottom of the first cup. Repeat with the other piece, filling the bottom layer. Then fill the second cup the same way. Checkpoint: The cookies should feel soft and slightly moistened, not drenched or bone-dry.

Apply Cream Layer 1 (2 minutes): Spoon roughly ¼ cup of the sweetened yogurt cream over the top of the cookies in the first cup, spreading it to the edges to seal the cookies in and create an even layer. This prevents moisture loss and holds everything together. Repeat with the second cup. Checkpoint: Each cup's cream should reach the cookies completely and be smooth on top.

Build Layer 2 (3 minutes): Repeat the dipping and layering process with the remaining ladyfingers. Take 1.5 to 2 more pieces, dip each for 1 second per side in the espresso, and place them on top of the yogurt cream in each cup. Again, the espresso is cold, so don't worry about cooking the yogurt—you're just adding flavor and moisture to the cookies.

Top Cream & Compress (3 minutes): Divide the rest of the yogurt cream evenly between both cups, spooning it on top of the second cookie layer and smoothing it flat with the back of a spoon or a small offset spatula. Now, gently tap each cup flat onto your countertop a few times (about 3–4 gentle taps)—you'll feel and sometimes hear small air bubbles escape. This settles the layers and removes hidden pockets of air that could make the texture less smooth. Checkpoint: The cups should feel slightly heavier and more compact, and the cream should be level across the top.

The Cold Cure (4+ hours or overnight): Cover both cups tightly with plastic wrap. Transfer them to the refrigerator for at least 4 hours. Overnight (8–12 hours) is highly preferred because the cookies will fully soften, the flavors will meld, and the texture will be closest to traditional tiramisu. You can make these up to 2 days ahead. Checkpoint: When you remove the cups from the fridge, they should be thoroughly chilled. The yogurt will be set but still creamy (not icy).

The Finish (1 minute): Just before diving in, hold a small fine-mesh strainer (a tea strainer works too) over one cup and dust the top generously with unsweetened dark cocoa powder. Tap the strainer gently so the powder falls evenly—you want a visible, attractive layer. Repeat with the second cup. The cocoa adds a bitter note that balances the sweetness and brings you that classic tiramisu experience. Checkpoint: Both cups should have a beautiful cocoa powder coat on top.