By Mollie Zapata, Eat. Run. Read.
Adapted from Brown Eyed Baker
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For the Cookies
1 1/2 cups all-purpose flour
3/4 cup cake flour
1 teaspoon baking powder
1/2 teaspoon salt
1 cup granulated sugar
Zest of 1 grapefruit
1/2 cup unsalted butter, at room temperature
2 egg yolks
1/2 cup grapefruit juice (freshly squeezed)
For the Filling
1/2 cup unsalted butter, at room temperature
2 3/4 cups powdered sugar
1 teaspoon grapefruit zest
3 tablespoons grapefruit juice (freshly squeezed)
1 small drop red or pink food coloring (optional)
1. Make the Cookies: In the bowl of your mixer (or in a large bowl using a hand mixer), rub together the sugar and grapefruit zest with your fingertips until the zest is evenly distributed and all of the sugar has been moistened.
2. Add the butter to the bowl and beat on medium speed until the mixture is light and fluffy, about three minutes. Add the egg yolks and beat until combined, scraping down the bowl as necessary.
3. Reduce the speed to low and add the flours, baking powder, and salt in three batches, alternating with the grapefruit juice, beginning and ending with the flour.
4. Mix just until the dough comes together. Transfer the dough to a piece of plastic wrap, pat it into a 1-inch disk, wrap in the plastic wrap and refrigerate for at least 30 minutes, or until firm (overnight is fine).
5. Preheat oven to 350 degrees F. Line two baking sheets with parchment paper or a silicone baking mat. Just spraying the pans isn’t enough here! Be warned, they will stick!
6. Roll out the dough on a lightly floured surface to about 1/8-inch thick. Use a 2-inch round cutter (I used a wine glass and a heart-shaped cutter), to cut out as many cookies as possible and transfer them to the prepared baking sheets, spacing them 1-inch apart. Gather together the dough scraps and repeat to get as many rounds as possible. Refrigerate the baking sheets (with the cookies on them) for 15 minutes.
7. Bake the cookies until just barely golden brown around the edges and still very light in color in the middle, about 12 minutes. Immediately remove the cookies to a wire rack and cool completely before assembling.
8. Make the Filling: Beat together the butter, powdered sugar and grapefruit zest on medium speed until light and fluffy, about five minutes. Add the grapefruit juice and food coloring (if using), increase the speed to medium-high and beat until smooth.
9. Assemble the Cookies: Match up the cookies by size, then spread or pipe on about 1 tablespoon of filling onto the flat side of half the cookies. Top with the matching cookie and press down slightly so the filling is pushed to the edges. Store in an airtight container and serve at room temperature.