Print
clock clock iconcutlery cutlery iconflag flag iconfolder folder iconinstagram instagram iconpinterest pinterest iconfacebook facebook iconprint print iconsquares squares iconheart heart iconheart solid heart solid icon
chocolate orange sandwich cookies.

Chocolate Orange Sandwich Cookies

5 Stars 4 Stars 3 Stars 2 Stars 1 Star No reviews
  • Author: Sally McKenney
  • 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

  1. 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.
  2. 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. 
  3. 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.
  4. 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.
  5. Preheat the oven to 350°F (177°C). Line large baking sheets with parchment paper or silicone baking mats.
  6. 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.
  7. 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.
  8. Allow cookies to cool on the baking sheet for 5 minutes, then transfer to a cooling rack to cool completely before filling.
  9. 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).
  10. 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.
  11. Store cookies in an airtight container at room temperature for up to 3 days or in the refrigerator for up to 1 week.

Notes

  1. 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.
  2. 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
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. Be sure to check out my top 5 cookie baking tips AND these are my 10 must-have cookie baking tools.
  8. The recipe is adapted and reprinted with permission from the beautiful cookbook The Cookie Book by Rebecca Firth.

Find it online: https://sallysbakingaddiction.com/chocolate-orange-sandwich-cookies/