Tiramisu Whoopie Pies

My neighbor brought over a plate of these after I mentioned missing the tiramisu from a little bakery that closed down last year. She handed them to me still cold from her fridge, dusted with cocoa, and said they were an experiment. One bite and I was texting her for the recipe before I even finished chewing. The soft chocolate cookies melted into that coffee-spiked mascarpone cream in a way that felt both familiar and completely new.

I made my first batch for a potluck brunch and watched three people go back for seconds before the savory dishes even came out. Someone asked if I'd ordered them from a bakery, which might be the highest compliment I've ever gotten. The key is not skimping on the espresso powder in the filling (it needs that bold coffee punch) and chilling everything properly so the cream doesn't squish out the sides.

Ingredients

• All-purpose flour (210 g): Gives structure to the soft cookies without making them cakey or dry.
• Unsweetened cocoa powder (55 g plus extra for dusting): Use good quality Dutch-process if you have it for a richer, less bitter chocolate flavor.
• Baking powder and baking soda: The combination gives just enough lift while keeping the cookies pillowy and tender.
• Salt (1/4 teaspoon): Balances the sweetness and deepens the chocolate taste in a way you'll notice if you leave it out.
• Unsalted butter (115 g, softened): Let it sit at room temperature until your finger leaves an indent, this makes creaming with sugar much easier.
• Granulated sugar (200 g): Creams with the butter to create air pockets that keep the cookies light.
• Large egg: Binds everything together and adds moisture, make sure it's at room temp so it incorporates smoothly.
• Vanilla extract (1 teaspoon): Enhances both the chocolate and coffee notes without competing with them.
• Whole milk (240 ml): The fat content keeps the cookies soft, low-fat milk will give you a drier result.
• Mascarpone cheese (225 g, chilled): The star of the filling, it's creamy and slightly sweet with a tang that cream cheese can't replicate.
• Heavy cream (120 ml, cold): Whips into the mascarpone to make the filling light and spreadable.
• Powdered sugar (60 g, sifted): Sweetens without graininess, sifting prevents lumps in your silky filling.
• Instant espresso powder (1 tablespoon): Dissolve it completely in hot water or you'll get bitter specks in the cream.
• Hot water (1 tablespoon): Just enough to bloom the espresso powder and release its full flavor.

Instructions

Prep your oven and pans:

Preheat to 350°F and line two baking sheets with parchment paper. This prevents sticking and makes cleanup almost nonexistent.

Mix the dry ingredients:

Whisk together flour, cocoa powder, baking powder, baking soda, and salt in a medium bowl until no streaks of cocoa remain. Set this aside while you work on the wet ingredients.

Cream butter and sugar:

Beat softened butter and granulated sugar in a large bowl with an electric mixer until the mixture looks pale and fluffy, about 3 minutes. Scrape down the sides of the bowl, then beat in the egg and vanilla until smooth.

Combine wet and dry:

Add the dry ingredients in three additions, alternating with the milk and starting and ending with dry. Mix on low speed until just combined, the batter will be thick and glossy.

Scoop and bake:

Drop 24 mounds of batter onto your prepared sheets using a cookie scoop or tablespoon, spacing them about 2 inches apart. Bake for 10 to 12 minutes until the tops spring back when lightly touched, then cool on the pans for 5 minutes before transferring to a wire rack.

Make the coffee filling:

Dissolve espresso powder in hot water and let it cool to room temperature. In a clean bowl, beat mascarpone, cold heavy cream, and sifted powdered sugar until smooth and thick (stop before it looks grainy). Gently beat in the cooled espresso and vanilla, then chill for 20 minutes if the filling seems too soft to spread.

Assemble the whoopie pies:

Match up cookies by size, then spread or pipe a generous dollop of filling onto the flat side of half the cookies. Top with the remaining cookies to create sandwiches, pressing gently so the filling reaches the edges without squishing out.

Finish and chill:

Dust the tops with unsweetened cocoa powder using a fine sieve for an even coating. Refrigerate for at least 30 minutes before serving so the flavors meld and the filling firms up just enough to hold its shape.

Save

The first time I served these at a dinner party, someone said they tasted like the lovechild of a whoopie pie and an Italian coffee bar. That description stuck with me because it's exactly right, they're playful and nostalgic but also grown-up and a little bit fancy. Now I make them whenever I want to impress someone without spending all day in the kitchen.

Storage and Make-Ahead Tips

These actually improve after a night in the fridge, the cookies soften slightly and absorb some of that coffee flavor from the filling. Store them in an airtight container in the refrigerator for up to two days, though they rarely last that long in my house. You can bake the cookies a day ahead and keep them wrapped at room temperature, then fill them a few hours before serving. If you want to get fancy, add a tablespoon of coffee liqueur to the filling for a boozy twist that tastes incredible with espresso.

Substitutions and Variations

If you can't find mascarpone, you can use cream cheese, but the flavor will be tangier and less delicate. I've tried it both ways and mascarpone is worth hunting down if you can. For a dairy-free version, I haven't tested it myself, but a friend swears by coconut cream and vegan cream cheese in the filling. You could also skip the cocoa dusting and drizzle melted dark chocolate over the tops for a more dramatic presentation.

Serving Suggestions

These shine at brunches, afternoon coffee dates, or as a plated dessert with a little whipped cream on the side. I like serving them with a strong cup of espresso or a glass of dessert wine if it's evening. They're rich enough that one per person is usually plenty, though I won't judge anyone who sneaks a second.

• Pair with a shot of espresso or a cappuccino to double down on the coffee vibes.
• Serve on a platter dusted with extra cocoa for a elegant presentation.
• Wrap individually in cellophane tied with ribbon for sweet homemade gifts.

Save

Every time I pull these out of the fridge and see that cocoa-dusted top, I get a little thrill. They're proof that you don't need a special occasion to make something that feels special.

Recipe FAQs

→ Can I make these whoopie pies ahead of time?

Yes, these whoopie pies can be assembled and stored in an airtight container in the refrigerator for up to 2 days. The filling may soften slightly over time, but they remain delicious.

→ What can I substitute for mascarpone cheese?

You can substitute cream cheese for mascarpone if it's unavailable, though the flavor will be tangier and less authentic to traditional tiramisu. The texture will also be slightly different.

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

Make sure your mascarpone and heavy cream are well-chilled before mixing. Avoid overbeating the filling, and if it seems too soft, refrigerate it for 20 minutes before assembling the whoopie pies.

→ Can I add alcohol to these whoopie pies?

Absolutely! For a boozy twist similar to traditional tiramisu, add 1 tablespoon of coffee liqueur such as Kahlúa or Tia Maria to the mascarpone filling for enhanced depth of flavor.

→ Why did my chocolate cookies spread too much while baking?

If your cookies spread excessively, your butter may have been too soft or melted. Ensure butter is softened but still holds its shape, and make sure your baking powder and baking soda are fresh for proper leavening.

→ Do I need to use instant espresso powder?

Instant espresso powder provides the strongest coffee flavor, but you can substitute with instant coffee granules. Just note that the coffee flavor may be slightly less intense than with espresso powder.