Prepare pudding mix according to package directions. Fold in whipped topping. Cover and chill.
Preheat oven to 375°.
Unroll phyllo dough on a large cutting board or work surface. Cut phyllo dough in half lengthwise. Carefully wrap and refreeze one half of dough for use in another recipe. Using scissors, cut remaining dough half crosswise into 3 (4 1/2 x 4-inch) rectangles.
Working with 1 phyllo dough section at a time (cover remaining dough with a towel to keep from drying), place 1 (4 1/2 x 4-inch) phyllo rectangle on work surface; coat with cooking spray and sprinkle with 1/2 teaspoon sugar. Place second phyllo rectangle on top of sugared phyllo sheet at a 45° angle; coat with cooking spray, and sprinkle with 1/2 teaspoon sugar. Continue procedure until you have a 6-layer stack of phyllo dough.
Carefully press prepared phyllo dough stack into a 6-ounce custard cup coated with cooking spray. Repeat procedure with remaining phyllo dough.
Place custard cups on baking sheets. Bake at 375° for 13 minutes or until golden brown. Immediately remove phyllo shells from custard cups; cool completely on wire racks.
Stir berries into mousse, reserving some berries for garnish. Spoon 1/3 cup mousse evenly into each phyllo shell. Sprinkle evenly with reserved berries.