Chocolate Peppermint Sandwich Cookies

Inspired by the iconic Oreo, these sandwich cookies combine cocoa powder, peppermint extract, and crushed candy canes for some festive winter flavor. This is a cut-out cookie, and you’ll notice the rolling method is like that used for Soft Sugar Cookies. For the chocolate version, use cocoa powder instead of flour to dust your surface and rolling pin, so that the sticky dough stays dark and workable.'

MAKES 28 SANDWICH COOKIES

SKILL LEVEL: Intermediate

PREP: 1 hour 10 minutes

BAKE: 11 to 12 minutes per batch

TOTAL: 3 hours 30 minutes, including chilling

INGREDIENTS

Sally's Baking 101: Foolproof Recipes from Easy to Advanced Sally McKenney

For the Cookies:

• 1½ cups all-purpose flour, plus more as needed (188g)

• ¾ cup unsweetened natural or Dutch-process cocoa powder, plus more as needed (64g)

• 1 teaspoon baking powder

• ⅛ teaspoon salt

• 12 tablespoons unsalted butter, at room temperature (170g)

• 1 cup granulated sugar (200g)

• 1 large egg, at room temperature

• ½ teaspoon vanilla extract

• ½ teaspoon peppermint extract

For the Peppermint Buttercream:

• 10 tablespoons unsalted butter, at room temperature (140g)

• 2¾ cups powdered sugar (330g)

• 2 tablespoons milk, at room temperature

• 1 teaspoon vanilla extract

• ½ to ¾ teaspoon peppermint extract

• ⅛ teaspoon salt

For the Garnish:

• ½ cup crushed peppermint candy canes (60g)

• 4 ounces semi-sweet or bittersweet chocolate, chopped (113g)    

DIRECTIONS

1. Make the cookies: In a medium bowl, whisk the flour, cocoa powder, baking powder, and salt.

2. In a large bowl using a handheld or stand mixer fitted with the paddle, beat the butter and sugar on high speed until the mixture is light and creamy, about 3 minutes. Add the egg, vanilla, and peppermint extract and beat on high speed until combined, about 1 minute. Scrape down the sides of the bowl as needed. Add the flour mixture and mix on low speed until combined. The dough should be soft. If it seems too soft and sticky for rolling, add 1 tablespoon more flour.

3. Divide the dough in half. Lightly dust a rolling pin and a piece of parchment paper or a silicone baking mat with cocoa powder. Roll out each half of the dough to about ¼-inch thickness; any shape is okay. Sprinkle lightly with cocoa powder if the dough seems too sticky.

4. Lightly dust one of the rolled-out dough portions with cocoa powder. Place the second rolled-out dough portion, still on the parchment paper, on top of the first. Cover the dough tightly and refrigerate it for at least 2 hours or up to 2 days.

5. Preheat the oven to 350°F (177°C). Line baking sheets with parchment paper or silicone baking mats.

6. Remove the top piece of dough from the refrigerator. Using a 2-inch round cookie cutter, cut the dough into rounds. Gather the scraps, reroll, and continue cutting until all the dough is used. Repeat with the second piece of dough. Arrange the cookies 2 inches apart on the prepared baking sheets.

7. Bake for 11 to 12 minutes or until the edges of the cookies are set. Cool the cookies on the baking sheet for 5 minutes before transferring to a cooling rack to cool completely.

8. Make the peppermint buttercream: In a large bowl using a handheld or stand mixer fitted with the paddle, beat the butter on medium speed until creamy, about 2 minutes. Add the powdered sugar, milk, vanilla, ½ teaspoon of the peppermint extract, and the salt. Beat on low speed for 30 seconds, then increase to medium-high speed and beat for 2 full minutes. Taste and beat in another ¼ teaspoon peppermint extract, if desired. Pipe or spread the peppermint buttercream over the bottom side of a cooled chocolate cookie, bringing it all the way to the edges. Place a second chocolate cookie on top, bottom side facing the filling, to make a sandwich. Repeat with the remaining cookies and buttercream.

9. Garnish the cookies: Put the crushed peppermint candy in a shallow dish. Roll the edges of the sandwich cookies in the crushed candy pieces, to coat the exposed buttercream.

10. Melt the chocolate. Drizzle the tops of the cookie sandwiches with melted chocolate. Refrigerate for 20 minutes or until the chocolate has set. Store covered tightly in the refrigerator for up to 5 days.

Reprinted with permission from Sally's Baking 101: Foolproof Recipes from Easy to Advanced by Sally McKenney. Copyright © 2025 by Sally McKenney. Published by Clarkson Potter, an imprint of the Crown Publishing Group, a division of Penguin Random House LLC, New York.

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