
These dark chocolate raspberry sandwich cookies turn basic ingredients into a fancy dessert that's perfect for any special event. The combo of rich chocolate shortbread with fluffy raspberry buttercream strikes just the right taste balance and looks just as good as it tastes.
I whipped these up for my sister's wedding shower, and they were gone before all other sweets. The pretty pink filling next to the dark chocolate cookies made them totally photo-worthy, not just yummy.
Ingredients
- For Cookies
- Unsalted butter: Softened to make cookies tender
- Truvia Sweet Complete All Purpose Sweetener: Gives just the right sweetness without using sugar
- Vanilla extract: Makes the chocolate taste even better
- Kosher salt: Brings out both sweet and chocolate flavors
- Large egg: Holds everything together and builds structure
- Dutch process cocoa powder: Gives that deep chocolate kick; go for quality brands
- All purpose flour: Makes the cookie base just right
- For Raspberry Buttercream
- Fresh or frozen raspberries: For real flavor and gorgeous pink color
- Truvia Sweet Complete All Purpose Sweetener: Cuts through the sour notes
- Water: Helps make the raspberry sauce
- Unsalted butter: Softened for super fluffy frosting
- Truvia Confectioners Sweetener: Keeps frosting smooth without sugar crystals
- Vanilla extract: Boosts the raspberry taste
- Heavy cream: Tweaks thickness for easy piping
- Pinch of salt: Cuts sweetness and lifts flavor
How To Make Dark Chocolate Raspberry Cookie Sandwiches
- Mix the chocolate cookies:
- Start by beating butter and Truvia Sweet Complete until it's smooth in your stand mixer. This'll take about 2 minutes at medium. Make sure your butter isn't cold for best results. Toss in vanilla and salt, mixing until they're all blended. This sets up your cookie's flavor base. Add the egg and mix till it's all combined, making sure to scrape the bowl so everything mixes evenly.
- Make the chocolate dough:
- Put in sifted cocoa powder and mix slowly until it's all blended. Sifting stops lumps for the smoothest dough. Slowly add flour half a cup at a time, mixing until the dough balls up around the mixer paddle. The dough might look too dry at first but keep mixing. If it's still too dry, add tiny splashes of milk, half a tablespoon at a time.
- Flatten and cool the dough:
- Put dough on parchment paper and cover with another sheet. Roll it between the paper until it's between quarter and half inch thick. This way it won't stick without needing more flour. Slide the rolled dough onto a cookie sheet, keeping the paper. Chill for a full hour so it gets firm enough to cut cleanly.
- Shape and bake the cookies:
- Take out chilled dough and cut circles with a 2 inch round cutter. Put cut cookies on a parchment-lined baking sheet with an inch between them. They'll hold their shape without spreading. Chill the cut cookies 15 more minutes while your oven heats to 350 degrees. Bake 9-10 minutes until edges firm up. Let cool on sheets 5 minutes then move to a wire rack.
- Cook raspberry sauce:
- Put raspberries with Truvia Sweet Complete and water in a pot over medium heat. Stir often, mashing berries against the pot to break them down. Keep cooking until the mix gets thick enough to coat a spoon. Strain through a fine mesh strainer to get rid of seeds and cool all the way. This gives strong raspberry flavor without gritty seeds.
- Whip up buttercream:
- Beat softened butter until it's pale and fluffy for about 2 minutes. Slowly add Truvia Confectioners Sweetener on low speed till it's mixed in. Turn speed up to medium-high and beat 2-3 minutes until it gets lighter. Add your raspberry sauce and salt to taste, one spoon at a time till you get the color you want. Adjust thickness with heavy cream or more sweetener if needed. Beat on high one last minute until it's super light and fluffy.
- Put cookies together:
- Fill a piping bag with a big star tip with your buttercream. Pipe a fancy swirl onto the flat side of one cookie and top with another cookie, pressing gently to make a sandwich. The star tip makes a pretty pattern you can see from the sides. Chill your finished cookies so the filling sets before serving, which also lets the flavors blend together.

The raspberry filling really makes this recipe special. I found that leaving the cookies in the fridge overnight lets moisture from the filling soften the cookies just a bit, creating an amazing contrast between the soft cookie and creamy center.
Storage Tips
These sandwich cookies will stay fresh up to 5 days when kept in a sealed container in the fridge. The filling actually stops the cookies from drying out. If you want to store them longer, you can freeze the finished cookies for up to a month. Just put them between sheets of parchment in a freezer container and let them thaw in the fridge overnight before eating.
Flavor Variations
While raspberry makes a beautiful match with the chocolate cookies, you can easily switch things up with other fruit sauces. Try blackberry for a deeper purple filling or strawberry for a softer pink. You might also play around with adding flavors like almond or orange to the buttercream for different taste combos. If you love chocolate, just mix a spoonful of cocoa powder into the buttercream for a chocolate-raspberry filling.
Serving Suggestions
These fancy cookie sandwiches deserve to be shown off. Set them up on a tiered plate for parties or bridal showers. They go really well with champagne for celebrations or afternoon tea. For a dessert table, arrange them in circles on a round plate to look like a flower, showing off the pink filling. During holiday season, brush the edges with some edible gold dust for extra pop.

Frequently Asked Questions
- → What should I do if the dough cracks?
If the dough feels crumbly, mix in small amounts of milk—about ½ tablespoon at a time—until it's smooth. Go slow to avoid overdoing it.
- → Is it okay to use frozen fruit for the buttercream?
Absolutely! Frozen raspberries work just fine. Let them defrost before blending, and drain off extra juice to keep the frosting firm.
- → Can I swap the sweetener for sugar?
Regular sugar is a great alternative. The exact amount may vary, so taste and adjust until it's just right.
- → How should I store these cookies after baking?
Keep the cookies in a sealed container at room temperature, or refrigerate if it's warm. Let them sit out before eating to soften.
- → Can I get the dough ready in advance?
You can! Make the dough early and chill it for up to 2 days in the fridge, or freeze it longer. Defrost slightly before using.
- → What other fillings could I use?
Feel free to try chocolate ganache, vanilla frosting, or something tangy like cream cheese frosting for a different spin.