In a medium saucepan, combine the granulated sugar, unsweetened cocoa powder, cornstarch, and salt. Whisk these dry ingredients together thoroughly to break up any large clumps of cocoa. This ensures that your pudding will be perfectly smooth without any grainy pockets of starch or powder.
Gradually pour the milk into the saucepan while whisking constantly. Place the pan over medium heat and continue to stir. Cook the mixture for about 8 to 10 minutes, or until it reaches a gentle boil. Once it begins to bubble, keep whisking for another minute as it thickens to a glossy, custard-like consistency.
Remove the saucepan from the heat. Stir in the butter and the alcohol-free vanilla extract until the butter is completely melted and the pudding is fragrant. Pour the warm pudding into six individual glass cups or ramekins. Place a piece of plastic wrap directly onto the surface of the pudding to prevent a skin from forming, then refrigerate for at least two hours or until completely cold.
In a chilled mixing bowl, beat the heavy whipping cream and powdered sugar together until stiff peaks form. Be careful not to over-beat the cream, as you want it to remain light and fluffy for the “fur” and “pom-pom” parts of the Santa hat.
Once the pudding is set, remove the plastic wrap. Pipe or spoon a thick circle of whipped cream around the top edge of each cup. Place a hulled strawberry, point-side up, in the center of the whipped cream ring. Finally, add a small dot of whipped cream to the tip of the strawberry to complete the look of a festive Santa hat.
