Get Ready to Bake: Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper to prevent sticking.
Mix Dry Goodies: In a small bowl, whisk together the flour, cocoa powder, baking powder, and salt. Set this aside for a moment.
Cream Wet Goodies: In a large mixing bowl (or using a stand mixer), beat the softened cream cheese and butter together until they are smooth and creamy.
Sweeten It Up: Add the granulated sugar to the cream cheese mixture and beat until everything is well combined and fluffy.
Add Eggs & Vanilla: Mix in the eggs one at a time, then stir in the vanilla extract. Scrape down the sides of the bowl to make sure everything is fully incorporated.
Combine Wet & Dry: With your mixer on low speed, gradually add the dry flour mixture to the wet ingredients. Mix just until a soft, chocolatey cookie dough forms. Don't overmix!
Scoop & Shape: Use a cookie scoop or a rounded tablespoon to portion out the dough. For a smoother look, gently roll the dough into balls with slightly wet or nonstick-sprayed hands. Place them onto your prepared baking sheet.
Bake to Perfection: Pop the cookies into the preheated oven and bake for 10-12 minutes. They should look set but still soft. Let them cool on the baking sheet for about 5 minutes before carefully transferring them to a wire rack to cool completely.
Whip Up the Icing: In a small microwave-safe bowl, combine the chocolate chips, butter, and milk. Microwave for 30 seconds, then stir well. Continue microwaving in 15-second bursts, stirring after each, until the chocolate is fully melted and smooth.
Sweeten the Glaze: Stir in ¾ cup of the sifted powdered sugar. If the icing seems too thick, add a couple more tablespoons of milk to thin it out. If it's too thin, add a bit more powdered sugar until it reaches a nice dipping consistency.
Glaze & Enjoy: Once the cookies are completely cool, dip the tops of each cookie into the chocolate icing. Place them on a piece of parchment or wax paper, icing side up, and let the icing set and harden to a beautiful, satiny finish.