Midnight Mint Hamantaschen

This hamantaschen is based on my  recipe for Thin Mints. For recreating the beloved Girl Scout cookies, I favor a recipe from Martha Stewart for deep dark chocolate espresso cookies. If you use extra dark Dutch process cocoa (like Hershey’s extra dark cocoa) to make the cookies, and then coat the baked cookies in minty chocolate, you get a pretty good approximation of Thin Mints.

I decided to turn this cookie concept into hamantachen, using a mint truffle as the filling. For the mint truffle filling, I tried out a recipe from Ruth’s Kitchen.

Result: the cookies like to explode open in the oven (as do many hamantaschen doughs), but otherwise, the recipe worked out perfectly. As with all hamantaschen, you have to be careful to seal the edges well. Even if the sides of the hamantaschen fall open during baking, the chocolate filling will stay put. Don’t overbake, because you don’t want to burn either the delicate chocolate filling or the cookie itself (it is hard to tell doneness from appearance with such a dark dough).

Chocolate Midnight Mint Truffle Hamantaschen

Extra Dark Chocolate Dough
Adapted from Martha Stewart’s Chocolate Espresso Dough. UPDATE: mint extract added, coffee powder taken out and amount of sugar increased for a mintier, less bittersweet dough. Additionally, I have added the option of dipping the hamantaschen in chocolate for more of a Girl Scout cookie effect.
1 1/2 cups all-purpose flour (6.75 ounces)
1/2 cup Hershey’s Extra Dark Cocoa (or extra dark Dutch process cocoa) (1.5 ounces)
1/4 tsp. salt
1 1/2 tsp. coffee powder
1/2 tsp. mint extract
1 cup butter or margarine (8 ounces)
1 cup powdered sugar (4 ounces) 1 1/2 cups powdered sugar (6 ounces)
1 tsp. vanilla

mint truffle filling (see below)

12-16 ounces bittersweet chocolate (I used Rose of Galilee bittersweet, which is a chocolate bark, and it worked perfectly), melted, for dipping cookies (optional)

In a bowl, combine the flour, cocoa, and coffee powder. In another bowl, cream the butter and sugar. Add the vanilla. Mix in the flour/cocoa mixture. Chill the dough (Place it on parchment paper, flatten it to 1/4″, fold it up in the paper, and chill until hard).

Roll out the dough on the parchment paper until it is 1/8″ thick.  Chill the dough until hard. Cut out 3″ circles. Place the circles on a parchment lined sheet pan. Fill each circle with a tsp. or so of filling (the below filling should be evenly divided among the cookies–the yield should be 2 dozen).

Pinch together three sides of the circle of dough to form a triangle. It the dough is sticky, refrigerate it until it is more manageable. Make sure that the sides are well pinched together–these will fall apart in the oven otherwise. Chill the shaped hamantaschen in the freezer before baking. I firmly believe freezing helps the cookies keep their shape during baking.

Bake the hamantaschen at 350 degrees for 15 to 20 minutes, or until the dough and filling is set. You can’t tell by color with these. Check at 15 minutes and see if the surface of the dough seems evenly dry and set. Touch the surface lightly to check.

Optional step: dip the baked cookies in melted chocolate and set the cookies on parchment while the chocolate hardens. This really gives the Girl Scout Thin Mint cookie effect.

yield: about 2 dozen

Mint Truffle Filling
Adapted from Ruth Reingold’s French Chocolate Truffles
6 ounces semisweet or bittersweet chocolate
2 ounces margarine or butter or coconut oil
2 egg yolks
1/4 tsp. mint extract

Melt chocolate and margarine in a double boiler (don’t leave out the margarine–I forgot to add it once and the chocolate seized when I added the rest of the ingredients). Whisk in yolks and extract. Let cool. When thickened, can scoop out spoonfuls for filling hamantaschen. If you refrigerate the filling to thicken it more quickly, check on it frequently, because it can get very hard and become difficult to scoop. (In retrospect, it would have been better to let the truffle mixture set up on a parchment or plastic wrap lined 8″x8″ pan and then have cut the hardened filling into squares that could be rolled into balls.)

If the filling gets hard, use a melon ball scoop to scoop out balls of chocolate truffle mixture. Roll the hardened filling into balls. Make 2 dozen balls, or enough to fill all the circles of dough.

For other hamantaschen flavors and baking tips:
Basic recipe and baking tips
Peanut Butter Chocolate Hamantaschen
Lemon Curd Filled Hamantaschen
Darth Vader Hamantaschen
Angelina Ballerina Hamantaschen
Hamantaschen Apple GaletteFruit Tart Hamantaschen
Hamantaschen Puff Pastry Shells
Hamantaschen French Toast Casserole

Ima on the Bima has some interesting links, too.

Tags: chocolate, cookies, hamantaschen, hamantashen, Purim