Mini Homemade Oreos With Vanilla And Pomegranate Filling

Homemade Oreos

When I worked at Flour, the Oreo cookies were my nemesis.

Homemade Oreos

Actually, even before I got the job, those cookies hassled me. I had to go in for trail, and I couldn't for the life of me cut straight through the thick log of chocolate dough. Luckily the hiring decision didn't rest on that one task. I got the job, and each day, after I had weighed, scooped, rolled, baked, and plated most of the other kinds of cookies, I'd get out the big knife, a cutting board, and those menacing logs of dough. They had to be just the right temperature. If the dough was too cold, it would just crumble and break. Too warm and it would mush against the cutting board, and I'd have some pretty oddly shaped cookies. Over time and with a lot of internal frustration, I got better and better, and eventually, I could pretty regularly turn out evenly cut cookies.

But that was only one-third of the battle. There was also the baking of the cookies to contend with. Being that they're already dark in color, it's tough to tell when chocolate cookies are ready. You can't just eyeball them to see if they're golden brown. And how long they're baked is important. Bake them too long, and they taste burnt. Underbake them, and they're too soft to hold up to the filling. You start to learn by smell and touch because you can't trust sight.

And then comes the last third of the battle. The cookies need just the right amount of filling. You don't want to underfill them -- that would throw off the cookie to filling ratio. And while I may think that gobs and gobs of filling is just perfect for me, that doesn't make for a nice lookin' Oreo either. So armed with a piping bag, each day I would work on piping just the right amount of filling on each Oreo bottom, so when I capped the bottoms with the tops, the filling would push out just to the edges.

So while I worked at Flour, if you asked me if I ever thought I'd make the Oreos at home, I would have given you a loud and clear "N-O." But I've had five months to recover now, and I considered myself ready to take on these cookies at home. And I didn't decide to make these to test my Oreo-making abilities (to make sure I still had "it"), but rather, the idea came to me after POM sent along some POM Concentrate for me to play around with.

I started flipping through cookbooks, saw the Oreos, thought about the imminence of Valentine's Day and the gorgeous pink filling I could make with a little POM Concentrate, and I couldn't get the idea out of my head.

Mini Homemade Oreos With Vanilla And Pomegranate Filling (adapted from Flour: Spectacular Recipes from Boston's Flour Bakery + Cafe)
(A printable version of the cookies and vanilla frosting is available on Boston.com)

Note: I call these mini cookies because they are much smaller than the ones at Flour, but they actually turned out to be about the size of a normal cookie. I divided the dough in half to make two logs and sliced these more thinly than the original recipe instructed. Next time I would even divide the dough in thirds and make three skinnier logs. 



1 1/2 cups (210 grams) flour
3/4 cup (90 grams) unsweetened cocoa powder
1/2 teaspoon baking soda
1 teaspoon kosher salt
1 cup (2 sticks) unsalted butter, melted
3/4 cup (150 grams) sugar
1 teaspoon vanilla extract
1 cup (200 grams) high-quality semisweet chocolate chips, melted
1 egg


In a small bowl, combine the flour, cocoa powder, baking soda, and salt. Set aside.

In a medium bowl, whisk together butter and sugar until combined, and then whisk in the vanilla and melted chocolate. Add the egg, and stir until well blended.

Using a wooden spoon, stir the flour mixture into the chocolate mixture.

Let the dough sit out at room temperature for 1 hour.

Divide the dough in half, and place each piece on a long sheet of parchment paper.

Shape one piece into a rough, long, skinny log. Place the log about one-third of the way down the parchment.

Pull the parchment over the log, and tuck it where it hits the front of the log. Using a bench scraper, push the parchment farther under the log. Move from side to side, and push with the bench scraper to even out the log.

Roll the rest of the parchment around the log. Repeat with the other half of the dough.

Refrigerate the dough for at least 2 hours, or until it is firm. Make sure to keep turning the logs so they don't get flat on the bottom. (You can refrigerate the logs overnight, but make sure you take them out of the fridge about an hour before slicing them, so they can soften back up enough to cut through them.)

Preheat oven to 325 degrees. Line 2 baking sheets with parchment paper.

Remove the dough from the paper, and cut the logs into thin slices, between 1/8- and 1/4-inch thick.

Place the slices on the baking sheets about 1 inch apart.

Bake the cookies for 15 to 17 minutes, turning them every 5 minutes. Lightly touch the center of a cookie to test for doneness. It should feel a little firm to the touch. (The cookies will still harden as they cool.)

Transfer cookies to cooling racks and cool completely. Continue baking the rest of the slices, and cool those completely as well.

Match cookie slices of similar sizes into pairs of tops and bottoms, and lay them out on cooling racks or cool sheet pans, turning the bottoms over so they are bottom-side up.

Vanilla Filling (adapted from Flour: Spectacular Recipes from Boston's Flour Bakery + Cafe)


1/2 cup (1 stick) unsalted butter, at room temperature
1 teaspoon vanilla extract
1 2/3 cup confectioners’ sugar, sifted
1 tablespoon milk
Pinch salt


In bowl of electric stand mixer fitted with paddle attachment, beat the butter on low speed for 30 seconds. Add the vanilla and confectioners sugar, and beat until smooth. Add the milk and salt, and beat until combined and completely smooth.


1/2 cup (1 stick) unsalted butter, at room temperature
1 2/3 cup confectioners’ sugar, sifted
2 to 3 teaspoons POM Concentrate (to taste)
2 drops pink food coloring (optional)


In bowl of electric stand mixer fitted with paddle attachment, beat the butter on low speed for 30 seconds. Add the confectioners sugar, and beat until smooth. Add POM Concentrate, and beat until combined and completely smooth. Mix in pink food coloring if desired.

For half of the cookies, scoop the vanilla filling into a piping bag fitted with a small round or star tip. Pipe around the outside and into the center of each cookie bottom.

Place the tops on, and press them down lightly to push the filling out to the edges.

Repeat with the pomegranate filling for the remaining cookies.

(You may need a second batch of one kind of filling in order to fill all of your cookies, depending how many you get.)

Store the cookies in an airtight container for up to 3 days.

Have you had the Flour Oreos? Have you ever made your own Oreos?