Using a paring knife, cut one corner of a caramel, about halfway up the side. Repeat with opposite corner to form a point on the bottom center of the candy. Place caramel on its side and roll back and forth on work surface to smooth. Repeat with remaining caramels.
Place frosting in a resealable plastic bag and snip one corner with scissors. Apply small dots of frosting on top of each cookie and place a baking piece on the frosting dots.
Cover flat tops of caramels with frosting. Place cookies on caramels, baking pieces up, to make acorn shapes.