Line a baking sheet with parchment paper and set aside.
In a mixing bowl, add the creamy peanut butter and sifted powdered sugar. Whisk or stir until the mixture is smooth and well combined. It should be thick but spreadable.
Lay out 32 Ritz crackers on a clean surface, flat side down. Spread a small amount of the peanut butter mixture onto half of the crackers, leaving a little space around the edges.
Top each filled cracker with another cracker to form a sandwich. Gently press together so they stick. Place the peanut butter cracker sandwiches onto the parchment-lined baking sheet.
Transfer the baking sheet to the freezer and chill the sandwiches for about 30 minutes, until the filling is firm.
While the sandwiches chill, place the milk chocolate chips in a heatproof bowl set over a pot of gently simmering water (double boiler). Stir frequently until the chocolate is completely melted and smooth. Remove from heat.
Remove the chilled cracker sandwiches from the freezer. Using a small pair of tongs, a fork, or tweezers, dip each sandwich into the melted chocolate, turning to coat it completely.
Let any excess chocolate drip off, gently shaking or tapping on the side of the bowl, then place the coated sandwich back onto the parchment-lined baking sheet.
Repeat with the remaining sandwiches until all are coated in chocolate.
Allow the cookies to sit at room temperature until the chocolate is fully set and dry to the touch, about 1 hour. You can place the tray in the refrigerator to speed up the setting time if desired.
Once the chocolate is set, carefully peel the cookies off the parchment. Serve and enjoy.