Place phyllo shells on a cookie sheet and heat in oven according to package directions.
Let cool on cookie sheet while you prepare filling.
In a medium mixing bowl, add the cream cheese and whipped topping. Beat with an electric mixer on low speed for about 1 minute.
Add the powdered sugar and mix on medium speed until light and fluffy.
Place filling in a pastry bag or Ziploc bag with the corner snipped off.
Sprinkle phyllo cups with powdered sugar.
Pipe the filling into each cup.
Top each pastry cup with your choice/combination of berries.
Sprinkle with more powdered sugar.