Microwave chocolate and 1 cup COOL WHIP in microwaveable bowl on HIGH 2 to 2-1/2 min. or until chocolate is almost melted. Stir until chocolate is completely melted and mixture is well blended. Stir in extract. Refrigerate until cooled.
Meanwhile, heat phyllo shells as directed on package. Cool.
Fill phyllo shells with chocolate mixture; top with remaining COOL WHIP and cherries. Refrigerate10 min.