Bourbon-O's (Chocolate Sandwich Cookies with Bourbon Cream)

October 3, 2014

Test Kitchen-Approved

Author Notes:

I've updated the classic sandwich cookie with a hearty swig of bourbon for a boozy touch -- but just to keep everyone happy, this recipe is designed so that half the filling stays booze-free. I usually stay clear of vegetable shortening in my baking, but in this recipe it really is essential to make the filling creamy and smooth. If you are truly averse, however, butter is a fine substitute.


Makes: 2 dozen sandwich cookies


For the cookies:

  • 1 1/4 cups flour
  • 1/2 cup unsweetened cocoa powder
  • 3/4 teaspoon baking soda
  • 1/4 teaspoon baking powder
  • 1/4 teaspoon espresso powder
  • 1/4 teaspoon salt
  • 8 tablespoons unsalted butter, softened
  • 3/4 cup sugar
  • 1 egg
  • 1/4 teaspoon vanilla extract

For the filling:

  • 4 tablespoons unsalted butter, softened
  • 1/4 cup vegetable shortening
  • 2 cups plus 1/3 cup powdered sugar
  • 1 vanilla bean, seeds scraped
  • 1 teaspoon vanilla extract
  • 2 teaspoons bourbon
In This Recipe


  1. Sift together flour, cocoa powder, baking soda, baking powder, espresso powder, and salt in a medium bowl and set aside.
  2. In a large bowl, beat the butter and sugar together in a large bowl until combined. Add the egg and vanilla and beat until smooth. Add flour mixture and stir with a wooden spoon until all the flour is incorporated.
  3. Wrap the dough in plastic and gently press it into a disk. Refrigerate for at least an hour (and up to several days).
  4. When you are ready to bake the cookies, preheat the oven to 350° F and line a baking sheet with parchment. On a lightly floured surface, roll out the dough, dusting with more flour if needed, to about 1/4 to 1/8 inch thick. Use a round 1 1/2-inch cookie cutter to stamp out as many cookies as possible and reroll the scraps as necessary. Bake for 7 to 9 minutes or until the tops have set and no longer look wet. Transfer to a wire rack and let cool completely.
  5. Meanwhile make the filling: In a large bowl beat together butter and shortening until combined. Add 2 cups powdered sugar and beat for several minutes until smooth. Add the vanilla extract and seeds and mix until incorporated.
  6. Transfer about half the filling to a small bowl -- this is your booze-free filling. Add the bourbon and 1/3 cup powdered sugar to the remaining filling and beat until combined - this is your booze filling.
  7. Use an offset spatula to spread a small amount of frosting on the bottom side of half of the cookies. Place the remaining cookies on top and gently squeeze each sandwich together to spread the filling to the edges. Filled cookies can be stored in an airtight container in the fridge for several days.

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Reviews (5) Questions (0)

5 Reviews

Michael December 17, 2018
I made these cookies today for a work event tomorrow, so fun to make. They are delicious, like really delicious! I did not split the filling in two, I made the total filling with the bourbon.<br /><br />Two recommendations: I like bourbon, my coworkers like bourbon...2 teaspoons did not pack a bourbon punch, I put in a total of 8 teaspoons of bourbon. <br /><br />I found the 1 1/2” diameter cutter too small, next time I will try the 2”.<br /><br />I will make these again before Christmas.<br />
candice B. April 12, 2015
These were so nice to make! Placing the perfect little circles on the pan and squishing them together later, I could make them all day. And honestly, they taste so amazing!
Amber B. March 22, 2015
I just made these. Fantastic! 5 stars! Dough was easy to work with and tastes great. Just the right texture. The bourbon in the filling is subtle though. So if you want the bourbon to be more readily identifiable, you may want to kick it up a notch.
Ann M. December 18, 2014
Just read your whole comment on shortening, I will substitute butter.
Ann M. December 18, 2014
Can I substitute butter for shortening in the filling?