In a medium saucepan, whisk together the sugar, cornstarch, cocoa powder, coffee powder, and salt. Gradually whisk in the whole milk and heavy cream, bringing to a low boil over medium-high heat. Boil for two minutes, whisking constantly. Remove from heat and whisk in the milk chocolate and vanilla extract. Stir until completely smooth.
Transfer pudding to a medium bowl and cover with plastic wrap (allowing the wrap to touch the surface to prevent a skin to form on the pudding). Chill for two hours, or until the pudding is set.
In the bowl of an electric mixer, whisk the heavy cream at medium-high. As it thickens, add in the powdered sugar, peppermint extract and food coloring. When soft peaks form, fold in the crumbled sandwich cookies.
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Layer pudding and whipped cream in serving dishes (or in one large dish). Sprinkle the top with crumbled cookies and enjoy!
Notes- I was cautious with the peppermint extract, because too much mint is no fun at all. Feel free to (carefully) add a little more than the recipe calls for. I also might add a little more green color next time. I also tossed in a couple extra Oreos, but that just depends on your preference.
If you want to make the original recipe, just use 1 teaspoon of pure vanilla extract in the whipped cream instead of peppermint. Eliminate the food coloring, and use regular Oreos.
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