Recipe adapted from Gourmet
If you like things on the sweeter side, I'd advise upping the sugar to 1/2 cup. If not, then stick with the 1/4 cup sugar.
2 tablespoons instant coffee granules
1 teaspoon of Dutch processed cocoa powder
2 tablespoons plus 2 teaspoon cornstarch
1/4 cup plus 2 tablespoon sugar, divided
1/2 cup heavy cream
1 teaspoon pure vanilla extract, divided
Cinnamon for sprinkling
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.
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), 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.
Adrianna Note: Be sure to scrap the corners of the pot with your whisk to ensure all the cornstarch is properly combined.
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 Saran wrap on the surface to stop that from happening. If you're a freak and love it, then by all means keep it uncovered.
While the pudding is chilling, beat cream with 1/2 teaspoon of vanilla and remaining 2 tablespoon sugar using an electric mixer just until soft peaks form. Spoon whipped cream onto puddings and dust cream lightly with cinnamon.
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!