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1
Do a little prep action by making your ice bath first. Grab two metal or glass bowls, one slightly smaller than the other. Fill the larger bowl with ice and a bit of water and place the smaller bowl inside it.
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2
Whisk together milk, coffee granules, cocoa powder, 1/2 teaspoon of vanilla extract, cornstarch, 1/4 cup sugar (or 1/2 cup of sugar-your choice depending on how sweet you like it), and a small pinch of salt in a heavy medium saucepan. Bring to a boil over medium heat, stirring occasionally, then boil 1 minute, whisking constantly. *Note: Be sure to scrape the corners of the pot with your whisk to ensure all of the cornstarch is properly combined.
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3
Transfer the pudding to the smaller bowl in your ice bath so it can cool, stirring often, about 10 minutes. If there are lumps in the pudding, simply run it through a sieve or strainer. Then pour the pudding into cups or ramekins and chill for 20 minutes. Since I really despise any skin on my pudding, I placed a piece of plastic wrap on the surface to stop that from happening. If you're a freak and love the skin, then by all means keep it uncovered.
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4
While the pudding is chilling, beat cream with the remaining 1/2 teaspoon of vanilla and 2 tablespoons of sugar using an electric mixer just until soft peaks form. Spoon whipped cream onto puddings and dust cream lightly with cinnamon.
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5
If you keep the pudding in the fridge overnight or even for a few hours, I'd take it out of the fridge 15 minutes before serving. I found the consistency was the best when it wasn't super cold. Enjoy!
