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These Halloween-themed pudding “dirt” cups have the spooky addition of black cocoa whipped cream plus white spiderwebs. The spiderwebs are easy: you pipe them over a crushed-ice bath so they set almost immediately. For the best results, be sure to flatten the surface of the crushed ice as much as possible before piping the webs. Little “spiders” made from sugar-coated gummy bears complete the eerie effect.
6 clear cups or glasses (each 9 fluid ounces), a piping bag and a medium round tip (or a resealable plastic bag with one corner snipped off)
Whisk together the instant pudding mix and milk in a large bowl until smooth. Let sit until slightly set, 5 minutes.
Whip the cream in another large bowl with an electric mixer on medium-high speed until soft peaks form, about 2 minutes. Add the cocoa powder and mix on high speed until stiff peaks form, about 1 minute. Transfer one-third of the whipped cream to the pudding and whisk until fully incorporated, then carefully fold in the remaining whipped cream with a rubber spatula.
Divide half of the pudding mixture among 6 clear cups or glasses (each 9 fluid ounces), filling them about halfway. Top each cup with 1 heaping tablespoon of the crushed cookies, then nestle 2 or 3 gummy worms and 3 or 4 candy eyeballs into the “dirt,” against the side of the cup so they are visible. Layer each cup with another heaping tablespoon of the crushed cookies and about 1/3 cup of the remaining pudding, then finish with 2 more heaping tablespoons of the crushed cookies. Refrigerate at least 1 hour.
Line a baking sheet with kitchen towels. To make the spiderwebs, fill a large bowl with crushed ice and a small amount of water. Press the ice down so the surface is as flat as possible. Transfer the melted wafers to a piping bag fitted with a medium round tip (or a resealable plastic bag with one corner snipped off). Pipe into the ice bath 4 intersecting lines to create a 3-inch asterisk, then pipe a circle just inside the asterisk and a smaller circle inside the first circle. Let the spiderweb set for 10 to 15 seconds then gently transfer to the prepared baking sheet. Repeat to make 8 spiderwebs; since they are fragile it is good to have a couple extra.
To make the spiders, arrange the gummy bears flat-side up. Use kitchen shears to snip 3 narrow triangles out of each short end, creating 4 legs on both sides of each spider.
Place a spiderweb on each dirt cup then top with a gummy spider. Serve cold.
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