Combine the cocoa powder, sugar, cornstarch, chocolate chips, and salt in a large tall pot. Whisk together and turn the heat on medium heat.
¾ cup semi-sweet chocolate chips, 1¼ cups granulated cane sugar, 6 Tablespoons cornstarch, ¼ teaspoon fine sea salt
Slowly stream in the cold milk while whisking at the same time to avoid clumping. Once all of the milk is poured in, whisk every 30-60 seconds to ensure the pudding mixture is being combined while the ingredients melt together.Be sure to scrape the bottom of the pan so that the chocolate chips do not stick to the bottom of the pot. 5 cups whole milk
Bring the pudding mixture to a gentle boil. You may need to increase the heat to get it to temperature. Allow the mixture to gently boil for 2-3 minutes while whisking every 10 seconds or nearly consistently. Add in the vanilla extract and whisk to combine.
2 teaspoons vanilla extract
The pudding will begin to thicken up*, cook for another minute longer before removing from the heat. Pudding should leave a thick layer on the back of a spoon and drip off in thick drops but not pour off. If pudding is still not thick enough, continue to cook on a gentle boil for a little bit longer whisking continuously. Whisk should form streaks in the pudding. Pour cooked pudding into a heat proof bowl.
Allow pudding to cool at room temperature for 10 minutes before covering directly with plastic wrap and moving to the refrigerator to chill for at least 4 hours. It's very important to cover the pudding with plastic wrap touching the surface of the pudding to avoid a skin layer from forming on top
Once the pudding has cooled and thickened in the refrigerator, using a food processor, pulse the cookies into fine crumbs leaving some chunks throughout (if desired). Alternatively, you can place the Oreos in a gallon plastic bag and crush them with a rolling pin or your hands into fine crumbly pieces.
25 Double Stuf Oreos
To assemble the dirt cups, use 6-8 ounce cups with lids. Add in a few tablespoons or ¼ cup of pudding, then 2 tablespoons of crushed Oreo crumbs, followed by another ¼ cup of pudding, topped with another layer of Oreo cookie crumbs. Place lid on the pudding cups and store in the refrigerator until ready to eat!
When ready to serve, add 3 gummy worms on top of each cup so that it appears they are coming out of the "dirt". Pudding should be served cold and stored in the refrigerator until ready to eat. Best enjoyed within 3 days.
24 gummy worms