In a medium mixing bowl, combine cream cheese, milk, cocoa powder, espresso powder, vanilla, and powdered sugar. Using an electric mixer, beat until combined and smooth, scraping down sides as needed.
Fold in Cool Whip until just combined.
Using a pastry bag or zip-top plastic bag with the corner cut off, pipe this mixture into the phyllo shells. Top with shaved chocolate or chocolate covered espresso beans as desired.
Best served immediately, but may be refrigerated 1-2 hours before serving if necessary.
Notes
Make ahead tip: You can make the filling and refrigerate it. Remove filling from refrigerator a half hour before serving to soften slightly. Fill phyllo cups and serve. Phyllo cups may get soggy if filled ahead of time.