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1. Preheat oven to 350 F. Combine the cocoa powder and water in a small bowl. Stir until thoroughly combined. Set aside to cool.
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2. In the bowl of a stand mixer fitted with a paddle attachment, cream the shortening and sugar. Add the cooled chocolate liquid, eggs and vanilla. Mix to combine.
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3. In a separate bowl, combine the flour, baking soda, baking powder and salt. Combine the milk and vinegar in a small measuring cup.
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4. Add 1/3 of the dry mixture into the chocolate mixture. Stir to combine. Stream in 1/2 of the milk mixture. Repeat and add another 1/3 of the dry mixture and the remaining milk mixture. Then add the last of the dry mixture and mix until creamy and smooth.
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5. Prepare 2 baking sheets by thoroughly greasing them with shortening. Spoon tablespoon size scoops of the chocolate batter onto the pan allowing 2 inches of room between each cookie.
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6. Bake at 350 F for 12 minutes.
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7. Remove pans from the oven, set them on a rack and allow cookies to cool for a few minutes. Then move the cookies onto a rack and allow them to cool completely.
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8. While the cookies are cooling, prepare the filling.
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9. In the bowl of a stand mixer fitter with a whisk attachment, cream the butter and cream cheese until fluffy. Add the vanilla, milk and salt. Whisk until combined. Slowly add in the sugar, 1/2 cup at a time. Add enough sugar to make the filling thick enough to hold together but not stiff; you should be able to form soft peaks.
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10. Spread the filling onto the bottom of one cooled cookie. Top with another cookie to create a sandwich. Place the assembled sandwich on a tray and repeat with the remaining cookies and filling.
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11. Place the sandwich cookies into the refrigerator for at least 20 minutes before serving in order to allow the filling to set.
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12. Store extra cookies in an airtight container in the refrigerator.
