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Melt the bittersweet chocolate in a double boiler or the microwave. Melt the white chocolate separately in a double boiler or the microwave.
Line 2 baking sheets with parchment. Stick 2 marshmallows on the end of each of 12 ice-pop sticks. Dip to fully coat the marshmallows in the bittersweet chocolate, then transfer to one of the prepared baking sheets. Let set slightly, about 3 minutes (enough so the crumbs will stick in the next step).
Dip the pops in the cookie crumbs to fully coat the bittersweet chocolate, then transfer to the second prepared baking sheet. Flash-freeze for 10 minutes to set the first layer. Line the first baking sheet with a new piece of parchment.
Dip the pops in the white chocolate to fully coat, then transfer to the re-lined baking sheet; let set for 3 minutes. Line the second baking sheet with a new piece of parchment.
Dip the pops in the cookie crumbs to fully coat the white chocolate, then transfer to the re-lined baking sheet. Flash-freeze again for 10 minutes to set.
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