Buttery shortbread cookies flavored with fresh orange zest and sandwiched with rich chocolate ganache, these chocolate orange sandwich cookies are reminiscent of Milano cookies. They’re soft, tender, fragrant, and simply unforgettable.
Back by popular demand! I originally published these chocolate orange sandwich cookies in 2017, and after many requests, my team and I recently republished it. The recipe is adapted from the beautiful cookbook The Cookie Book by Rebecca Firth. We made a few subtle tweaks along the way and added updated photos. I hope fans of the original are excited to bake them again!
If there’s one flavor combination that feels both bright and cozy, it’s orange and chocolate. We love it in orange chocolate chip ricotta cookies, and if you haven’t made these yet, you’re going to love it here too.
Think of these cookies as the citrusy cousin of classic butter cookies: buttery and crisp at the edges, soft in the center, and carrying that subtle citrus aroma that makes your kitchen smell like sunshine. And once you pair them with rich chocolate ganache? Absolutely irresistible.
Why These Cookies Became a Fan Favorite:
- Bright citrus + rich chocolate is a classic pairing that never disappoints.
- Tender, buttery cookies that are sturdy enough to sandwich but delicate when you bite in.
- Elegant, yet approachable. Very basic cookie dough and ganache steps.
- Make-ahead friendly. The flavor gets even better as the ganache settles and the orange oils bloom. The cookies become a little softer, for that melt-in-your-mouth moment that feels like pure indulgence.
Here’s What You Need for Chocolate Orange Sandwich Cookies
There’s no leavening, like with shortbread cookies, but there is egg, so the texture is more similar to spritz cookies or slice and bake cookies.
- Butter: The foundation of flavor and structure. Make sure it’s properly softened to room temperature before beginning.
- Confectioners’ Sugar: Like snowball cookies, we’re using confectioners’ sugar to sweeten; it keeps the texture smooth and tender.
- Orange Zest: You need the zest of about 1 large orange. If the oranges you can find are on the small side, get 2 to be safe.
- Vanilla Extract: More flavor! Try using homemade vanilla extract here, or vanilla bean paste.
- Egg: 1 egg adds structure and stability, so these cookies aren’t crumbly like shortbread cookies. An extra egg yolk adds richness and softness.
- Salt: To balance the sweetness and add flavor.
- All-Purpose Flour: Add the flour directly to the wet ingredients—no need for another bowl.
Plus, heavy cream and chocolate for the ganache.
Make the Cookie Dough First
This is a 1-bowl cookie dough! Creamed butter and sugar provide the base of the cookie dough, so you’ll need a mixer (either handheld or stand).
Expect a VERY Soft Dough
Roll out the cookie dough to around 1/4 inch thick. This is a very, very soft dough, so be sure to flour your work surface and rolling pin generously. Or you can roll the dough between two sheets of parchment paper.
I usually generously flour a silicone baking mat and roll the dough out on that. If you have difficulty rolling out dough to an even thickness, try this adjustable rolling pin. Speaking from experience—it’s incredibly handy!
Chill rolled-out cookie dough. Without chilling, these cut-out cookies won’t hold their shapes. Chill the rolled-out cookie dough for at least 3 hours, or up to 3 days.
Cut into circles. Choose a cookie or biscuit cutter that’s about 1.5 inches in diameter. I use the 1.5-inch fluted-edge cutter from this set. If you re-roll the dough scraps, you should get about 64 cookies of this size, to make 32 cookie sandwiches.
It’s optional, but I like to sprinkle a little sparkling coarse sugar on top of the cookies, for that little something extra!
While the cookies are baking, make the…
Chocolate Ganache Filling
The ganache needs time to thicken before you can use it, so get it going while the cookies are in the oven and cooling.
You need just 2 ingredients for the filling: heavy cream (aka heavy whipping cream or double cream) and pure chocolate. Look for the bars of baking chocolate near the chocolate chips in the baking aisle, typically sold in 4-ounce (113g) bars. I like Ghirardelli, Baker’s, and Lindt brands, in either semi-sweet or bittersweet.
To make the ganache, heat the heavy cream until it just starts to simmer, and then immediately pour it over the chopped chocolate. Let it sit for a few minutes to soften the chocolate, then stir until it’s completely combined, melted, and glossy.
If you want extra help with the chocolate ganache, see my chocolate ganache page. (But I promise it’s really easy!)
Let the ganache sit at room temperature for about 1 hour, until thickened to a pipeable consistency. (If your kitchen is warm, refrigerate it briefly, but don’t let it firm up too much.)
You can spread the ganache onto the cookies, but piping is quicker and neater. Pipe a dollop onto the flat side of half the cookies, then sandwich with the remaining cookies.
These cookies are wonderful the day they’re assembled, but even better on day 2 as the ganache sets and the cookies soften slightly for a bakery-style, melt-in-your-mouth texture.
Cheerful, elegant, and irresistibly soft, these chocolate orange sandwich cookies bring together bright citrus and rich chocolate in the best way!
Chocolate Orange Sandwich Cookies
- Prep Time: 3 hours, 30 minutes (includes chilling)
- Cook Time: 10 minutes
- Total Time: 2 hours
- Yield: 32 cookie sandwiches
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
Soft, buttery orange-scented cookies sandwiched with rich chocolate ganache, these chocolate orange sandwich cookies are soft, tender, and reminiscent of classic Milano cookies. Made with fresh orange zest and a simple two-ingredient ganache, they’re elegant, make-ahead friendly, and even better the next day as the flavors meld and the cookies soften. Have extra flour handy for rolling out the dough.
Ingredients
Cookies
- 1 cup (16 Tbsp; 226g) unsalted butter, softened to room temperature
- 1 cup (120g) confectioners’ sugar
- 1 and 1/2 Tablespoons fresh orange zest (about 1 large orange)
- 1 large egg, at room temperature
- 1 large egg yolk, at room temperature
- 1 and 1/2 teaspoons pure vanilla extract
- 1/4 teaspoon salt
- 2 cups (250g) all-purpose flour (spooned & leveled), plus more as needed for rolling
- optional: coarse sparkling sugar for topping
Chocolate Ganache
- 2/3 cup (160g/ml) heavy cream
- 6 ounces (170g) semi-sweet chocolate, finely chopped
Instructions
- Preliminary note: The chocolate ganache needs at least 45 minutes to thicken before it can be used in the cookie sandwiches. I recommend starting the ganache while the cookies are in the oven.
- Make the cookies: In a large bowl using a handheld or stand mixer fitted with a paddle attachment, beat the butter on medium-high speed until smooth and creamy, about 2 minutes. Add the confectioners’ sugar and orange zest, and beat until completely combined. Scrape down the sides and bottom of the bowl as needed. Add the egg, egg yolk, vanilla extract, and salt. Beat on medium-high speed until combined, scraping down the sides and bottom of the bowl as needed. Finally, add the flour and beat on low speed until incorporated, then gradually increase the speed until the dough comes together. The cookie dough will be very, very soft.
- Generously flour a rolling pin. Roll out the dough onto a very generously floured sheet of parchment paper or a silicone baking mat (I prefer the silicone mat) to about 1/4-inch thickness. The rolled-out dough can be any shape, as long as it is evenly 1/4-inch thick. (If it helps, place a piece of parchment on top of the dough before you roll it out, to keep the rolling pin from sticking to the dough.) Sprinkle with more flour as needed to prevent sticking.
- Place the rolled-out dough, with the parchment or mat underneath, onto a baking sheet and refrigerate for at least 3 hours and up to 2 days. If chilling longer than a couple hours, lightly cover with parchment paper or plastic wrap.
- Preheat the oven to 350°F (177°C). Line large baking sheets with parchment paper or silicone baking mats.
- Remove the dough from the refrigerator. Using a 1.5-inch round cookie cutter, cut into shapes. I used the 1.5 inch fluted round cookie cutter from this set. Re-roll the remaining dough and continue cutting until all is used. Arrange cookies on baking sheets 2 inches apart. If desired, sprinkle and lightly press some coarse sugar into the tops.
- Bake cookies for 9–11 minutes until very lightly browned around the edges. The cookies do not brown much on top. Rotate the baking sheets halfway through bake time.
- Allow cookies to cool on the baking sheet for 5 minutes, then transfer to a cooling rack to cool completely before filling.
- Make the ganache: Place chopped chocolate in a heat-safe bowl. Heat the cream in a small saucepan until it begins to gently simmer. (Do not let it come to a rapid boil—that’s too hot!) Pour over chocolate and let it sit for 2–3 minutes to gently soften the chocolate. Slowly stir until chocolate is completely melted and combined with the cream. Allow to cool and thicken until it’s a pipeable/spreadable consistency, at least 45 minutes, or up to 1.5 hours (depending on the temperature of your kitchen).
- Fit a piping bag with a large round tip, such as Wilton #12. (You can spread the ganache on with a knife if you don’t want to use a piping tip, but it can get pretty messy!) Fill the piping bag with the thickened ganache. Flip half of the cookies over and pipe a dollop of ganache onto the flat side. Top with the remaining cookies and gently press until the ganache spreads to the edges.
- Store cookies in an airtight container at room temperature for up to 3 days or in the refrigerator for up to 1 week.
Notes
- Make-Ahead Instructions: Chocolate ganache can be prepared, covered, and refrigerated for up to 3 days before using. Let it sit at room temperature to soften or microwave for 5–10 seconds before using. Plain (un-sandwiched) cookies freeze well for up to 3 months. Thaw overnight in the refrigerator. You can chill the rolled-out cookie dough in the refrigerator for up to 2 days (step 4). You can also freeze the cookie dough, before rolling out in step 3, for up to 3 months. Then allow to thaw overnight in the refrigerator and bring to room temperature before rolling out. Because the dough has already been freezing, chill for only 30 minutes in step 4 as opposed to 3 hours.
- Special Tools (affiliate links): Citrus Zester | Electric Mixer (Handheld or Stand) | Rolling Pin | Baking Sheets | Silicone Baking Mats or Parchment Paper | Fluted Round Cookie Cutters (I used the 1.5-inch cutter from that set) | Coarse Sugar | Cooling Rack | Saucepan | Glass Mixing Bowls | Piping Bag, Disposable or Reusable | Round Piping Tip
- Recipe Updates in 2025: The recipe was updated to make the orange butter cookies slightly sweeter, spread less, and to increase the amount of chocolate ganache for the filling. To make the cookies the way this recipe was originally written, decrease the confectioners’ sugar to 3/4 cup (90g), decrease the refrigeration time to 1 hour, and decrease the amount of chocolate ganache to 4 ounces (113g) chopped chocolate and 1/2 cup (120g/ml) heavy cream.
- Why Is The Dough Soft and Sticky? This dough is intentionally very soft for a tender cookie. Chilling the rolled-out dough is essential so the cookies hold their shape when cut and baked. When rolling and shaping, use plenty of flour.
- Can I Skip the Extra Egg Yolk? I don’t recommend it. The extra yolk adds richness and keeps the cookies soft rather than crumbly.
- Can I Add Orange Extract? The fresh zest provides plenty of flavor, but you can add 1/4 teaspoon orange extract if you’d like a stronger citrus note.
- Be sure to check out my top 5 cookie baking tips AND these are my 10 must-have cookie baking tools.
- The recipe is adapted and reprinted with permission from the beautiful cookbook The Cookie Book by Rebecca Firth.
Reader Comments and Reviews
Could I leave the orange out so its like a traditional Milano cookie?
Hi Ashley, absolutely!