Preheat oven to 350°F. Line baking sheets with parchment paper and set aside.
In a medium-sized bowl, combine flour, baking soda, and salt. Set aside.
In the bowl of your mixer, cream butter, peanut butter, and brown sugar on medium speed until smooth and fluffy, scraping the sides of the bowl as needed.
Beat in the egg on medium speed, then beat in the milk and vanilla, scraping the sides of the bowl as needed.
With the mixer on low, slowly add the flour mixture, beating until a smooth dough forms.
Using a medium cookie scoop, scoop dough and place cookies 2 inches apart.
Bake for 9 minutes, until edges just very barely start to turn golden.
Remove cookies from oven and immediately top with chopped peanut butter cups.
Let cookies cool on baking sheets for 5 minutes, then remove to wire rack to finish cooling completely.
Melt almond bark according to package directions.
Place wax paper under baking racks holding the cookies, and drizzle generously.
Let candy set up completely before serving.