Make candy cup. Flatten jumbo baking cup and place on cake board. Melt light cocoa Candy Melts candy according to package directions. Use brush to paint cup with melted candy, leaving 1/4 in. uncovered at edge.
Crumble several balls of aluminum foil, 3/4 in. dia. Place under outer edge of cup to form ruffled cup. Chill until firm, about 10 to 15 minutes. Repeat brushing with melted candy, if necessary.
Make pears. Poach pears until fork tender.
Assemble treat. Carefully peel baking cup from candy cup.
Position cooled poached pear in candy cup. Use caramel in a cut parchment bag to drizzle over pear.