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These chocolate raspberry Milano cookies are a delightful twist on the classic Milano cookies. Crisp, buttery chocolate cookies are sandwiched with a berry filling, making these cookies sinfully delicious!
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What makes this dish special
Years ago, I was determined to recreate a Milano cookie recipe at home. I tried a few times, but I could never quite nail that delicate, crispy texture or get the cookies to hold their shape. After a few failed attempts, I gave up on the idea entirely. But after learning more baking techniques over the years, I decided to give it another go.
This time, I wanted to make a different version of a Milano, and what could be better than making a chocolate Milano sandwiched with raspberry filling? The flavor combination is guaranteed to be a winner. After a couple of tries, I'm happy to say that I was able to successfully create chocolate raspberry Milano cookies I've been dreaming about. They're crisp, buttery, with just the right amount of chocolate, sweetness, and raspberry tartness.
For more classic cookies with a twist, check out my apple cider caramel stuffed snickerdoodles, matcha and white cookies, and kaya linzer cookies!
Ingredients
- Raspberries: The raspberries are cooked down to concentrate their flavor and release their natural juices, which then get combined with powdered sugar to create a sweet-tart frosting.
- Powdered sugar: In the cookie dough, it creates a tender, delicate crumb since powdered sugar dissolves more easily than granulated sugar. In the filling, it thickens the raspberry juice into a spreadable frosting.
- Egg white: The extra egg white (in addition to the whole egg) adds structure and helps create that characteristic crisp, light, and slightly airy texture that Milano cookies are known for.
- Cocoa powder: Gives the cookies their chocolate taste and dark color while keeping the batter light enough to pipe through a pastry bag.
- Milk: Adds moisture and helps bring the dough together to the right consistency for piping.
Substitutions and variations
- Fruit: Try these cookies with another fruit filling, such as strawberries or cherries.
- Filling: You can skip the fruit filling and sandwich the cookies with chocolate ganache for a decadent chocolate treat, or Nutella for a chocolate-hazelnut cookie.
Recipe
Chocolate Raspberry Milano Cookies
Ingredients
Raspberry filling
- 6 ounces raspberries
- 1 tablespoon granulated sugar
- ¾ cup powdered sugar (98 grams)
Chocolate milano cookies
- 11 tablespoons butter, softened at room temperature (155 grams)
- ½ cup powdered sugar (65 grams)
- ¼ cup granulated sugar (50 grams)
- 1 large egg, at room temperature
- 1 large egg white, at room temperature
- 1 ¼ cups all-purpose flour (156 grams)
- 2 tablespoons cocoa powder (10 grams)
- ½ teaspoon salt
- 1 tablespoon milk
- 1 teaspoon vanilla extract
Instructions
- Preheat oven to 350 degrees F. Line two baking sheets with parchment paper.
- Combine raspberries with 1 tablespoon granulated sugar in a medium pot. Bring to a boil over medium heat. Gently mash the berries to extract the juice and let simmer for 5 minutes. Remove from heat and strain, reserving the juices. Let cool completely.
- Meanwhile, make the cookie batter. Add butter, powdered sugar, and granulated sugar in the bowl of a stand mixer and beat together until creamed, about 3-4 minutes. Add egg and egg white, mixing until well combined.
- Sift together flour, cocoa powder, and salt and add to the cake batter, stirring just until combined. Add milk and vanilla extract and mix just until combined.
- Transfer cookie batter to a piping bag with a ½-inch round tip. Pipe 2 ½-inch long strips of batter onto the prepared baking sheets, leaving 2 inches of space in between the cookies.
- Bake cookies for 10 minutes. Rotate the sheet pans and continue baking for 5-8 more minutes or until the cookies are browned. Remove from the oven and let cool completely on the baking sheets. The cookies will crisp up as they cool.
- Combine 2 tablespoons of the reserved raspberry juice with ¾ cup powdered sugar, mixing until well combined. The frosting will be thick. Pipe frosting on the bottom of half of the cookies. Top with the remaining cookies, gently pressing them together.
Notes
Step-by-step instructions
Step 1: Prepare cookie batter
This chocolate raspberry Milano cookies recipe starts with making the raspberry filling, which is surprisingly simple. Combine raspberries with a tablespoon of granulated sugar in a pot and bring them to a boil over medium heat.
Gently mash the berries to release their juices, then let everything simmer for about 5 minutes. Strain the mixture to remove the seeds and pulp, reserving that beautiful ruby-red juice for later. Let it cool completely while you work on the cookies.
For the cookie batter, cream together softened butter with both powdered and granulated sugar until light and fluffy. This should take about 3-4 minutes.
The powdered sugar is key here for creating that tender, delicate texture. Add the egg and egg white, mixing until everything is well combined.
Then sift together the flour, cocoa powder, and salt, and gently fold them into the batter. Finish by stirring in the milk and vanilla extract just until combined. Don't overmix at this stage, or your cookies might turn out tough instead of tender.
Step 2: Bake
Transfer your batter to a piping bag fitted with a ½-inch round tip. Then, pipe 2½-inch long strips onto parchment-lined baking sheets, making sure to leave about 2 inches of space between each cookie since they'll spread slightly.
Recipe tip
Fold the parchment paper into 12 equal sections and draw a 2 ½-inch line in the center of each to guide you while you're piping the cookies.
The batter should be thick but still flow smoothly through the tip-if it's too stiff, you can add another teaspoon of milk.
Bake the cookies at 350°F for 10 minutes, then rotate your baking sheets and continue baking for another 5-8 minutes.
You'll know they're done when the cookies look set and are slightly browned around the edges. They might seem a bit soft when you first take them out, but they'll crisp up beautifully as they cool on the baking sheets.
This is crucial for getting that signature Milano snap.
Step 3: Assemble cookies
Once your cookies are completely cool, it's time to assemble them. Mix 2 tablespoons of that reserved raspberry juice with ¾ cup of powdered sugar until you have a thick frosting. The consistency should be spreadable but not runny.
Pipe or spread the raspberry frosting onto the flat bottom of half of your cookies, then gently press the remaining cookies on top to create sandwiches.
The frosting will soften the cookies slightly over time, so these are best enjoyed within a day or two. But honestly, they're so good that they probably won't last that long anyway.
After all those years of trying, I finally have my perfect homemade chocolate raspberry Milano cookies. And the chocolate raspberry combination makes them even better than the original!
Make-ahead and storage tips
- Make-ahead: You can make the cookie dough the day before and chill it in the refridgerator until ready to bake.
- Store: Store them in an airtight container at room temperature for 2-3 days. The filling will soften the cookies slightly over time, so they're best enjoyed within the first day or two.
Frequently asked questions
A piping bag gives you the classic Milano shape, but if you don't have one, you can use a zip-top bag with the corner cut off or carefully spoon small oval shapes onto the baking sheet.
The batter should be thick but pipeable. If it's too stiff, you can add another teaspoon of milk to loosen it slightly. Make sure your butter is properly softened to room temperature, as cold butter can make the batter too thick.
You can also freeze unfilled cookies for up to a month. Fill them closer to serving time for the best texture.
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Alicia F says
I never made cookies like these before but they came out so well! They were crisp with a snap and tasted so good with the raspberry filling. Thanks for the recipe!
Christine Ma says
I'm so glad you enjoyed them!