Recipe: Triple-Chocolate Peppermint Thumbprint Cookies

Recipes from The Kitchn

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Sometimes the time comes when you need to double down on the chocolate. Or triple down, perhaps. And what better time than during the holiday season to triple down on some good chocolate, especially when there's a silky peppermint filling involved and little shards of peppermint candy strewn on top?

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These cookies weren't really my idea, at least at the beginning. I'd seen a recipe in the Baked Explorations cookbook about a year ago for Chocolate Mint Thumbprint cookies and have been thinking about them ever since. We make thumbprint cookies in our family for the holidays, but usually rely on a relatively standard butter cookie, rolled in toasted nuts and filled with jam. They're delightful. But they're no Triple Chocolate Peppermint Thumbprint.

I began thinking about this recipe after looking at the recipe by the Baked crew, and I knew I wanted mine to be different. I wanted an even richer chocolate cookie and I wanted the filling to be chocolate as well, with just a kiss of mint, so it wouldn't be too overpowering. I tend to bake mostly with whole-grain flours at home, so I knew I wanted to experiment with a few favorites and I didn't want to skimp on the salt (chocolate and salt are always so wonderful together).

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And so we've arrived, ultimately, at a very different cookie than the one I was inspired by — mine is a delightful holiday cookie that lasted all of 1 1/2 days around our house (although we did have some visitors drop by). For flour, I ended up using a mixture of rye and spelt flours. Spelt flour, if you haven't had the chance to experiment with it at home, is a really easy whole-grain flour to substitute for all-purpose flour as it has a mild flavor and acts much like white flour in recipes. I combine it here with rye flour, which has fine texture and a dark, earthy flavor that I think pairs so well with chocolate.

The resulting cookies are soft and tender and full of flavor. I think you're going to like them. If you'd rather use all-purpose flour (or 100% spelt flour), please do. You could also use experiment with a mixture of all-purpose flour and whole-wheat flour if you'd like. I'm always a proponent of using what you have at home and making the recipe versus never making it because you feel intimidated by the ingredients or they're tough to come across (but if you can get your hands on rye flour, it really is delicious in this recipe).

As for the candy cane pieces: I made some cookies with crushed candy cane bits and some without. I can't decide which I like best. I suppose maybe there's an aesthetic decision to be had — but really, enough of that. There are cookies to make. And cookies to eat. Happy holidays!

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Triple-Chocolate Peppermint Thumbprint Cookies

Makes 16 to 18 cookies

For the cookies:
1 cup (145g) rye flour
3/4 cup (90g) spelt flour
1/3 cup (30g) unsweetened Dutch-process cocoa powder
1 teaspoon kosher salt
4 ounces bittersweet chocolate (at least 60% cocoa), chopped
2 ounces semisweet chocolate chips
1 cup (2 sticks) unsalted butter, room temperature
1/2 cup (120g) natural cane sugar (like turbinado), plus more for rolling
1 large egg, room temperature
1 teaspoon pure vanilla extract

For the filling:
4 ounces semisweet chocolate chips
3 tablespoons unsalted butter
1/2 teaspoon pure peppermint extract
Crushed candy canes, for garnish

In a medium mixing bowl, whisk the rye and spelt flour with the cocoa powder and salt. Set aside. In a microwave-safe bowl, melt the bittersweet and semi-sweet chocolates on low until just melted. Whisk well until smooth, then set aside to cool slightly.

In the bowl of a stand mixer fitted with the paddle attachment (or using an electric mixer), beat the butter until light and creamy, about 2 minutes. Add the sugar and beat on medium until fluffy, another 2 minutes. Add the egg and vanilla and beat until just combined. Pour the melted and slightly cooled chocolate into the mixer and beat just until incorporated.

Add the flour and cocoa into the mixer bowl in two rounds, beating at low speed in between each addition. Scrape the sides of the bowl as needed. Chill the dough in the refrigerator until firm enough to roll into balls, about 30 minutes. Meanwhile, preheat the oven to 350°F.

Line 2 baking sheets with silicone baking mats or parchment paper. Spoon the coarse sugar into a small, shallow bowl. Scoop up roughly 2 tablespoons of the chilled dough and form into balls. Roll in the coarse sugar and transfer to the baking sheets. Using your thumb or index finger, press down firmly into the center of each cookie to form an indentation. Bake the cookies for 12 to 14 minutes, or until dry on top and slightly firm. Once out of the oven, press down gently on the indentations again to reinforce them, and transfer the cookie sheets to racks to cool completely.

Meanwhile, make the filling: In a microwave-safe bowl, microwave the semi-sweet chocolate chips and butter until melted. Stir in the peppermint extract. Set aside until slightly thickened, about 5 minutes. Using a teaspoon and working neatly, spoon the chocolate filling into the indents in the cookie. Gently sprinkle crushed candy cane bits onto the center of the cookie if you like – or leave as is. Allow the filling to set at room temperature before serving, about 20 to 30 minutes. Cover leftover cookies in an airtight container for 2 to 3 days.

Recipe Notes

  • The cookies continue to firm up as they cool, so if they appear a bit soft to the touch right when you pull them from the oven, chances are they'll be perfect.
  • Coarse sanding sugar is even better than turbinado sugar for rolling the cookie dough balls because it won't melt in the oven and the cookies will look almost sparkly. I didn't happen to have any so I used a coarse turbinado, which was an ok stand-in.

Per serving, based on 16 servings. (% daily value)
Calories
295
Fat
19.8 g (30.5%)
Saturated
12.1 g (60.4%)
Trans
0.6 g
Carbs
30.8 g (10.3%)
Fiber
3.3 g (13.4%)
Sugars
17.7 g
Protein
3.5 g (6.9%)
Cholesterol
47.9 mg (16%)
Sodium
154.7 mg (6.4%)

(Image credits: Megan Gordon)