Chocolate Bourbon Hamantaschen with Bailey's Glaze
Recipe type: Dessert
Cuisine: Purim
Prep time: 
Cook time: 
Total time: 
Serves: 15-20
Boozy Chocolate Bourbon Hamantaschen cookies!
  • For Guinness hamantaschen:
  • ¾ cup granulated sugar
  • 1 stick (1/2 cup) butter, at room temperature
  • 1 egg, plus 1 for egg wash
  • 1 teaspoon vanilla extract
  • 4 tablespoons Guinness or stout beer
  • 2¼ cups all-purpose flour, sifted
  • 1 teaspoon baking powder
  • ½ teaspoon salt
  • For bourbon ganache filling:
  • ½ cup heavy whipping cream
  • 2 tablespoons bourbon (I used Bulleit)
  • 6 ounces semi sweet chocolate
  • 2 cups powdered sugar, sifted
  • For Bailey's drizzle:
  • 1 cup powdered sugar
  • 1-2 tablespoons Bailey's Irish Cream
  1. In a large bowl with an electric hand or stand mixer with whisk attachment, mix sugar and butter until light and fluffy, about 3 minutes. Then add in egg, vanilla and Guinness and mix until well combined. Then add in flour, baking powder and salt and mix just until combined and uniform. Dough will be just slightly sticky.
  2. Cover the dough and chill it in the refrigerator overnight. You can also freeze it at this point for future use for up to 2 months.
  3. To make ganache filling, in a medium sauce pan on low heat, heat heavy cream, bourbon, and chocolate until everything is well combined. Let cook for 1-2 minutes, remove from heat, whisk in powdered sugar and let cool in the refrigerator. Filling should be thick. You can freeze to speed up cooling if you like.
  4. When ready to bake, preheat oven to 350 degrees F.
  5. Roll out dough to ⅛ inch thin and cut into circles using a 3 or 3½-inch cookie cutter. Add a heaping teaspoon of the filling to the center of each hamantaschen. Fold in 3 corners to form a triangle and overlap the edges to seal. Don’t overstuff, or your hamantaschen may leak.
  6. Place hamantaschen on a parchment lined cookie sheet and freeze for 30 minutes to help seal the cookie so it won’t leak or spread. Whisk the remaining egg with a tablespoon of water and brush over hamantaschen.
  7. Bake 12-15 minutes until lightly browned on the bottom. While cookies are baking, stir together powdered sugar and just enough Bailey's to make a drizzle. Cool hamantaschen on cooling racks, drizzle with Bailey's drizzle and serve with Irish car bombs!
Also, you will need to chill the dough overnight.
Recipe by What Jew Wanna Eat at