Line a baking sheet with wax paper. Insert a lollipop stick into cream filling of each cookie.
Melt chocolate and shortening in a small bowl in microwave; stir until smooth.
Dip 1 cookie pop into melted chocolate, letting top of cookie rest on bottom of bowl for support. Spoon melted chocolate over cookie to coat. Transfer to lined baking sheet, using a fork to support pop from underneath if needed.
Sprinkle around edge with sprinkles, making a “wreath.” Add chocolate drops. Let stand until set. Repeat with remaining cookie pops, remelting chocolate as needed. Wrap in food-safe cellophane or plastic wrap; tie with bow for gift-giving.
Store: Refrigerator 2 weeks
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