For the Cookies:
Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat. Set aside.
In a large bowl, use a mixer to beat the softened butter and sugar together until creamy and light yellow in color (about 4-5 minutes).
Add the eggs one at a time, beating them into the butter and sugar mixture. Then, beat in the vanilla extract.
Sift in the flour, salt, and baking powder. Beat until well combined.
Portion the cookie dough into heaping tablespoons. Roll into balls and place onto the prepared baking sheet.
Press each ball down with the bottom of a drinking glass until flattened to just over ¼ inch thick.
Bake for 10 minutes. Remove from the oven and let cool for 2-3 minutes on the baking sheet before transferring to a wire cooling rack to finish cooling.
For the Glaze & Topping:
Stir the milk into the confectioner’s sugar until a thin, smooth frosting forms.
Divide the frosting into two bowls. Tint one bowl with pink food coloring and leave the other white.
Lay half of the cooled cookies face up on a wire cooling rack set over a baking sheet to catch any drips.
For frosting, you can drizzle the glaze over the cookies with a fork or transfer it to a small Ziploc bag and cut off a tiny corner. Drizzle the frosting over the cookies in a zigzag motion.
While the frosting is still wet, sprinkle the Strawberry Shortcake Crumbs on top.
Allow the frosting to fully dry before packaging or serving the cookies.