Tiramisu Whoopie Pies

My sister walked into the kitchen one afternoon holding a glossy cookbook, pointing at a picture of tiramisu whoopie pies like she'd just discovered gold. I was skeptical—chocolate cookies with coffee cream sounded fussy, maybe too precious for a weeknight. But the smell of cocoa baking in the oven and the way that mascarpone filling came together, silky and bold with espresso, made me a believer before I even tasted one. Now they're my go-to when I want something that feels special without the fuss of layering an actual tiramisu in a trifle dish.

I made these for a book club once, and every single person asked for the recipe before we even discussed the novel. One friend, who claimed she didn't like coffee desserts, ate three and admitted she'd been wrong about her own preferences. There's something about the bittersweet cocoa against the sweet, creamy filling that wins people over, even the skeptics.

Ingredients

• All-purpose flour: The backbone of the cookies, keeping them tender and cake-like without turning dense or dry.
• Unsweetened cocoa powder: Go for Dutch-process if you have it—it deepens the chocolate flavor and gives the cookies that dark, elegant color.
• Baking powder and baking soda: The duo that makes these cookies puff up soft and pillowy, not flat and crispy.
• Unsalted butter, softened: Let it sit at room temperature so it creams smoothly with the sugar, creating that airy texture.
• Granulated sugar: Sweetens and helps the cookies hold their shape while baking.
• Large egg: Binds everything together and adds richness to the batter.
• Vanilla extract: A quiet flavor anchor that rounds out the chocolate.
• Whole milk: Keeps the batter moist and tender, making the cookies soft instead of cakey and crumbly.
• Mascarpone cheese, chilled: The star of the filling, creamy and slightly tangy, just like real tiramisu.
• Heavy cream, cold: Whips into the mascarpone to make it light and fluffy, almost mousse-like.
• Powdered sugar, sifted: Sweetens without grittiness and helps stabilize the filling.
• Instant espresso powder: Dissolved in hot water, it delivers that bold coffee punch without watering down the cream.
• Unsweetened cocoa powder, for dusting: The final flourish that makes them look bakery-perfect and adds a hint of bitterness.

Instructions

Prep your pans:

Preheat the oven to 350°F and line two baking sheets with parchment paper. This keeps the cookies from sticking and makes cleanup a breeze.

Mix the dry ingredients:

Whisk together flour, cocoa powder, baking powder, baking soda, and salt in a medium bowl. Whisking aerates the cocoa and prevents lumps in your batter.

Cream butter and sugar:

Beat the softened butter and granulated sugar in a large bowl until light and fluffy, about 3 minutes. This step builds the structure and tenderness of the cookies.

Add egg and vanilla:

Beat in the egg and vanilla extract until fully combined and smooth. Don't rush this—you want everything evenly mixed.

Alternate wet and dry:

Add the dry ingredients in three parts, alternating with the milk, starting and ending with dry. Mix gently until just combined—overmixing makes tough cookies.

Scoop the batter:

Use a medium cookie scoop or tablespoon to drop 24 mounds onto your prepared sheets, spacing them about 2 inches apart. They'll spread slightly but hold their shape nicely.

Bake until springy:

Bake for 10 to 12 minutes, until the tops spring back lightly when touched. Let them cool on the pans for 5 minutes, then move to a wire rack to cool completely.

Make the espresso base:

Dissolve the instant espresso powder in hot water and let it cool to room temperature. Using it warm will melt the mascarpone and ruin the texture.

Whip the filling:

Beat mascarpone, cold heavy cream, and sifted powdered sugar until smooth and thick, being careful not to overbeat or it may turn grainy. Fold in the cooled espresso and vanilla until just combined.

Chill if needed:

If the filling feels too soft to spread, refrigerate it for 20 minutes. It should be thick enough to hold its shape between the cookies.

Assemble the pies:

Spread or pipe a generous dollop of filling onto the flat side of half the cookies, then sandwich with the remaining cookies. Press gently so the filling spreads to the edges without squishing out.

Dust and chill:

Dust the tops with unsweetened cocoa powder using a fine sieve for an even coat. Refrigerate for at least 30 minutes before serving so the filling sets and the flavors meld.

Pin it

The first time I packed these for a potluck, I watched a grown man close his eyes and sigh after his first bite. He told me it reminded him of his grandmother's tiramisu, which she only made on Christmas Eve. I didn't have the heart to tell him these were easier than her recipe probably was, but I did send him home with extras.

Choosing Your Cocoa

Dutch-process cocoa gives these cookies a smoother, less acidic flavor and a deeper, almost black color that looks stunning. Natural cocoa works too, but the taste will be sharper and the color lighter. I've made them both ways, and while I prefer Dutch-process for the elegance, natural cocoa won't ruin anything. Just don't skip sifting it—cocoa clumps are the enemy of smooth batter.

Storing and Serving

These whoopie pies actually improve after a day in the fridge, once the cookies soften slightly and soak up some of that coffee cream. Store them in an airtight container for up to two days, though I've never seen them last that long. If you're making them ahead, bake the cookies and whip the filling separately, then assemble a few hours before serving. They're best served cold, straight from the fridge, with the cocoa dusting still intact.

Ways to Make Them Your Own

If you want to lean into the boozy tiramisu vibe, stir a tablespoon of coffee liqueur into the filling—it adds depth without making them taste overtly alcoholic. You can swap mascarpone for cream cheese if that's what you have, but know the flavor will be tangier and less luxurious. I've also tried adding a pinch of cinnamon to the cookie batter, which gave them a subtle warmth that paired beautifully with the espresso.

• Brush the cookie tops lightly with espresso before dusting for extra coffee intensity.
• Sprinkle mini chocolate chips into the filling for a little crunch.
• Freeze assembled whoopie pies for up to a month and thaw in the fridge before serving.

Pin it

These little sandwiches prove you don't need a fancy dessert to make people feel cared for. Serve them cold, dust them generously, and watch them disappear faster than you thought possible.

Recipe FAQs

→ Can I make these whoopie pies ahead of time?

Yes, you can prepare the cookies up to 1 day in advance and store them unfilled in an airtight container. Fill them a few hours before serving for the best texture. Assembled whoopie pies keep well refrigerated for up to 2 days.

→ What can I substitute for mascarpone cheese?

Cream cheese can be used as a substitute, though it will create a tangier flavor profile. For best results, use full-fat cream cheese at room temperature and beat it until very smooth before adding other ingredients.

→ How do I prevent the filling from becoming too runny?

Make sure your mascarpone and heavy cream are well-chilled before whipping. Avoid overbeating, which can cause the mixture to separate. If the filling seems soft, refrigerate it for 20-30 minutes before assembling to achieve the perfect consistency.

→ Can I add alcohol to enhance the tiramisu flavor?

Absolutely! Adding 1 tablespoon of coffee liqueur, Marsala wine, or dark rum to the filling will deepen the authentic tiramisu taste. Just be mindful this makes them unsuitable for children.

→ What's the best way to dust cocoa powder evenly?

Use a fine-mesh sieve to dust cocoa powder over the assembled whoopie pies. Hold the sieve about 6 inches above and gently tap it to create an even, professional-looking finish.

→ Why are my cookies spreading too much during baking?

Ensure your butter is softened but not melted, and avoid overmixing the batter. Chilling the scooped dough for 15 minutes before baking can also help the cookies maintain their shape and achieve that characteristic dome top.