Preheat the oven to 400°F. Line baking sheets with parchment paper.

In the bowl of a stand mixer fitted with the paddle attachment, or in a large bowl with an electric mixer, cream together the shortening and sugar until light and fluffy.

Add in the egg, vanilla, buttermilk, and water and mix until the ingredients are fully incorporated.

In a medium bowl, whisk together the flour, baking soda, cocoa, and salt. Slowly add the dry ingredients to the shortening mixture and mix until just combined. Use a rubber spatula to gently fold the chocolate chips into the batter.

Use a medium cookie scoop (1.5 tablespoons) to drop batter onto prepared cookie sheets about 2 inches apart.

Bake for 8-9 minutes in the preheated oven.

Allow cakes to cool on baking sheets for 5 minutes before removing to wire racks to cool completely.

In the bowl of a stand mixer fitted with the paddle attachment, beat the butter on medium-high speed for 3-4 minutes.

Turn the mixer down to low speed and gradually add in the powdered sugar until thoroughly combined. Turn the mixer back up to medium-high speed and mix for 5 minutes.

Add in the cherry juice and vanilla and beat an additional 2 minutes.

Use a rubber spatula to fold the chopped cherries into the buttercream.

*Note If the buttercream is too thick, you can add a little milk in 1 teaspoon at a time until the desired consistency is reached.

Spoon or pipe the buttercream onto the flat sides of half the cookies and top with remaining cookies.