Overview

These generously sized cookie sandwiches are composed of light and moist chocolate cake and a lightly sweetened whipped cream filling.

Cookbook author Rose Levy Beranbaum suggests leaving the butter and egg on your kitchen counter for an hour to get them to the proper temperature. Superfine sugar is ideal for making this filling because it dissolves better; if you don’t have any, you can approximate the same texture by grinding granulated sugar in the food processor (use 1 cup of sugar, at least, for best results). If you prefer, you can fill the whoopie pies with buttercream or cream cheese frosting.

An instant-read thermometer, a kitchen scale and a 2-inch cookie scoop will come in handy for this recipe.

Make Ahead: The unfilled cookies can be stored in an airtight container at room temperature for 3 days, or refrigerate for up to 1 week. Wrap tightly in plastic wrap, seal in a zip-top bag and freeze for up to 3 months. The whipped cream can be made a few hours in advance and refrigerated (give it another quick whisk if it has deflated a bit). The filled cookies are best eaten right away, but can be refrigerated for up to 8 hours in an airtight container. You will have whipped cream filling left over.

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Ingredients

FOR THE COOKIES

1 12ounces(42 grams) dark chocolate, 60 to 62 percent, chopped

1cup(125 grams) bleached all-purpose flour

Scant 1/4 cup (19 grams) unsweetened Dutch-process cocoa powder (sift before measuring if using volume)

12teaspoonbaking powder

12teaspoonbaking soda

12teaspoonfine sea salt

2tablespoonsunsalted butter, at room temperature (see headnote)

2tablespoonscanola or safflower oil

12cupplus 1 tablespoon (120 grams) packed dark brown sugar

1large egg, at room temperature (see headnote)

12cupbuttermilk

FOR THE FILLING

1cupheavy cream

1tablespoonsuperfine sugar (see headnote)

1teaspoonvanilla extract


Steps

Step 1

Position a rack in the middle of the oven; preheat to 400 degrees. Grease two rimmed baking sheets with cooking oil spray.

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Step 2

About 30 minutes before you start to make the cookies, melt the chocolate in a microwave-safe bowl on HIGH in 15-second increments, stirring in between, until smooth. Let cool until the chocolate is no longer warm to the touch yet still fluid (80 to 85 degrees).

Step 3

Whisk together the flour, cocoa powder, baking powder, baking soda and salt in a mixing bowl. (If there are lumps from the cocoa powder or baking soda, sift the mixture.)

Step 4

Combine the butter, oil, dark brown sugar and egg in the bowl of a stand mixer; beat on medium speed for about 5 minutes, stopping to scrape down the sides of the bowl as needed. The mixture should be smooth and paler in color.

Step 5

Add the melted/cooled chocolate; beat on low speed until well incorporated.

Step 6

Add one-third of the flour mixture along with one-third of the buttermilk; beat on low speed until just incorporated. Stop to scrape down the sides of the bowl. Repeat with another third of the flour mixture and a third of the buttermilk, and then the final third. Increase the speed to medium; beat for about 15 seconds, until smooth.

Step 7

Measure the batter into a 2-inch cookie scoop, gently rounded, or use two spoons to drop 6 rounded mounds (about 42 grams each) of batter, evenly spaced onto one of the prepared baking sheets. The mounds should be about 2 inches wide by 1 inch high.

Step 8

Bake one sheet at a time (middle rack) for 6 minutes, rotating it from front to back. Then bake for 2 to 4 minutes, or just until the caky cookies spring back when pressed lightly with a fingertip.

Step 9

Allow the batch to cool (on the baking sheet) on a wire rack for 5 to 10 minutes. Then use a thin metal spatula to transfer the cookie cakes directly onto the rack to cool completely.

Step 10

Meanwhile, scoop the remaining batter onto the second baking sheet; repeat the baking and cooling steps.

Step 11

For the filling: Combine the heavy cream, superfine sugar and vanilla extract in a medium metal mixing bowl; a handheld electric mixer is easier for this amount of cream. Cover and refrigerate for at least 15 minutes; refrigerate the beaters of the handheld mixer as well. Beat the mixture, starting on low and gradually increasing the speed to medium-high as it thickens, until stiff peaks form.

Step 12

To assemble the whoopie pies, place a mound of the filling (about 3 rounded tablespoons) on the flat sides of 6 cooled cookies. Press the flat sides of the remaining 6 cookies lightly on top of the filling, just until the filling is forced to the edges. You will not use all the filling.

Serve right away, or refrigerate for up to 8 hours.

Adapted from “Rose’s Baking Basics: 100 Essential Recipes, With More Than 600 Step-by-Step Photos,” by Rose Levy Beranbaum (Houghton Mifflin Harcourt, 2018).

Tested by Becky Krystal; email questions to voraciously@washpost.com.

Scale and get a printer-friendly version of the recipe here.

Did you make this recipe? Take a photo and tag us on Instagram with #eatvoraciously.

Nutrition

Calories: 380; Total Fat: 21 g; Saturated Fat: 10 g; Cholesterol: 70 mg; Sodium: 290 mg; Carbohydrates: 44 g; Dietary Fiber: 2 g; Sugars: 25 g; Protein: 5 g.