01 - Whisk together sugar, cocoa powder, cornstarch, and salt in a medium saucepan.
02 - Gradually whisk in milk until the mixture is smooth and free of lumps.
03 - Place the saucepan over medium heat and cook, whisking constantly, until thickened and gently boiling, approximately 5 to 7 minutes.
04 - Remove from heat and stir in vanilla extract and chocolate chips until completely melted and smooth.
05 - Divide pudding into individual dishes, cover surface directly with plastic wrap to prevent skin formation.
06 - Refrigerate for at least 2 hours until fully set.
07 - In a chilled mixing bowl, beat cold heavy cream with powdered sugar and vanilla extract until soft peaks form.
08 - Top each chilled pudding serving with a dollop of the homemade whipped cream and serve immediately.