Super Stuffed Mint Chocolate Sandwich Cookies

Who doesn’t love a homemade “Oreo,” particularly a “double stuffed” one? A generous dollop of pale green minty filling is sandwiched between two crispy and uber-chocolate-y wafers, making these sandwich cookies nothing short of Easter-perfect. Tinting the filling pale pink and flavoring it with vanilla, would be equally as festive, as would putting half as much filling in each sandwich, for a more traditional “Oreo” eating experience.
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Double-Stuffed Mint-Chocolate Sandwich Cookies (aka Grasshopper “Double Stuf” Oreos . . . )

Who doesn’t love a homemade “Oreo,” particularly a “double stuffed” one? A generous dollop of pale green minty filling is sandwiched between two crispy and uber-chocolate-y wafers, making these sandwich cookies nothing short of Easter-perfect. Tinting the filling pale pink and flavoring it with vanilla, would be equally as festive, as would putting half as much filling in each sandwich, for a more traditional “Oreo” eating experience.
Recipe Author Jessie Sheehan
Servings 20 cookies

Ingredients

For the cookies:

  • 1 1/4 cups all-purpose flour (170 g)
  • 3/4 cup Dutch process cocoa powder (80 g)
  • 1/4 tsp baking soda
  • 1/2 tsp salt
  • 1/2 cup unsalted butter (113 g)
  • 1/4 cup vegetable shortening (45 g)
  • 1 1/4 cup granulated sugar (250 g)
  • 2 tsp pure vanilla extract
  • 2 tbsp light corn syrup

For the filling:

  • 1 1/2 cups vegetable shortening (260 g)
  • 1 tsp salt
  • 2 1/2 tsp peppermint extract or to taste
  • 6 cups confectioners' sugar, sifted if lumpy (600 g)
  • 2 tbsp water room temperature
  • A few drops of green gel food coloring
  • Mint-green sparkling sugar for decorating

Instructions

To make the cookies:

  • In a medium bowl, whisk together the flour, cocoa powder, baking soda and salt.
  • In the bowl of a stand mixer fitted with the paddle attachment, cream the butter, shortening, sugar, and vanilla on medium-low speed until fluffy, about 2 minutes. Scrape the sides of the bowl with a rubber spatula. Add the corn syrup and beat until just combined. 
  • Add the dry ingredients all at once to the mixer bowl and on low speed, beat until the dough just comes together. 
  • Place the dough on a piece of plastic wrap and form it into a log, about 2 1/4-in wide, rolling it along the counter in order to shape it into a perfect cylinder. Tighten the plastic wrap around it and refrigerate until firm, at least 2 hours or overnight.
  • Preheat the oven to 350-degrees. Line two baking sheets with parchment paper and set aside. 
  • Unwrap the chilled log and use a sharp paring or chef’s knife to slice it into 1/4-in thick rounds. Rotate the log as you slice, to avoid flattening one side. Arrange the slices on the prepared baking sheets.
  • Bake the cookies until they appear dry, about 12 minutes, rotating the sheets halfway through the baking time. Once removed from the oven, use a stiff metal or heatproof plastic spatula to press down lightly on each cookie to flatten it. Let cool before filling.
  • Repeat with the remaining cookies 

To make the filling:

  • Combine the shortening, salt and extract in the bowl of a stand mixer, fitted with the paddle attachment, and beat on medium speed just until smooth. Add the sugar and beat just until incorporated.  Add the water and food coloring and beat just until smooth and uniform in color. Do not overbeat if you would like a stiff, Oreo-like filling. If you want a fluffy filling, that oozes a bit when you take a bite, beat until fluffy.

To assemble the cookies:

  • Roll 3 tablespoons of filling in your hands to form a ball, and gently flatten the ball on to the underside of one cookie until it almost reaches the edge, place another cookie on top and press down gently. Wet your finger and run it around the edge of the cookie to smooth. 
  • Place the sparkling sugar in a small bowl and roll the cookie edge in it. Repeat with the remaining cookies. Serve at once or keep at room temperature covered in plastic wrap for up to 3 days, or in the freeze for up to one month.

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