Make filling: In a large bowl, combine vanilla pudding mix and milk and whisk until thick. Fold in Cool Whip and transfer mixture to a piping bag. Refrigerate until ready to use.
Make ganache: Add chocolate chips to a medium bowl. In a small saucepan over medium heat, heat heavy cream until bubbles form around the edges. Pour heavy cream over chocolate chips and let sit 2 minutes, then whisk until smooth. Let cool slightly.
Assemble pies: Pipe filling onto the flat side of a Nilla wafer then top with another Nilla wafer to create a sandwich. Repeat with remaining filling. Spoon ganache on top of each cream pie.
Recipe by 5* trending recipes with videos at https://food.theffeed.com/2020/04/01/mini-boston-cream-pies/