Preheat oven to 350°F (180°C). Line 2 baking sheets with parchment paper or silicone baking mats.
Whisk the flour, baking powder, and salt together in a medium bowl. Set aside.
In a large bowl using a handheld or stand mixer fitted with a paddle attachment, beat the shortening and sugar on medium-high speed until smooth and creamy, about 2 minutes. Add the eggs, one at a time, and vanilla extract, and beat on high speed until combined, about 1 minute.
Scrape down the sides and up the bottom of the bowl and beat again as needed to combine.
Reduce to low speed and add the dry ingredients in 3 additions, alternating with the milk. Beat everything on low until combined and no pockets of flour remain.
Using a greased 1/4-cup dry measuring cup, drop mounds of dough 4 inches apart on prepared baking sheets– 6 cookies per sheet. Make sure the cookies are uniformly round (I shape the cookie dough using lightly greased fingers).
Bake for 12-15 minutes or until the edges are lightly browned.
Allow cookies to cool on the baking sheets for 5 minutes, then transfer to a wire rack to cool completely before icing.
For the white frosting:
In the bowl of an electric mixer with a paddle attachment, beat 1 tablespoon butter, 1 cup of powdered sugar and 1/2 teaspoon of vanilla on medium speed for a couple of minutes, or until smooth.
With the mixer on low speed, add in the milk 1 tablespoon at a time and mix until combined. Add milk as needed until the frosting has reached the desired thickness to spread.
For the Chocolate frosting:
In the bowl of an electric mixer with a paddle attachment, beat 1 tablespoon butter, 1 cup of powdered sugar, 1/4 cup cocoa powder, and 1/2 teaspoon of vanilla on medium speed for a couple of minutes, or until smooth.
With the mixer on low speed, add in the milk 1 tablespoon at a time and mix until combined. Add milk as needed until the frosting has reached the desired thickness to spread.
Frosting the Cookies:
Halfmoon cookies are frosted on the flat side, or bottom of the cookie. Spread vanilla frosting onto half of the cookies on the flat side. Spread the chocolate icing onto the other side.
Notes
Cookies will stay fresh in an airtight container at room temperature for 2 days or in the refrigerator for up to 1 week.