01 - In a medium saucepan, whisk together sugar, cocoa powder, cornstarch, and salt until evenly combined.
02 - Gradually whisk in whole milk to the dry mixture until smooth and free of lumps.
03 - Place the saucepan over medium heat and cook, whisking constantly, until the mixture thickens and reaches a gentle boil, approximately 5 to 7 minutes.
04 - Remove from heat and stir in vanilla extract and semi-sweet chocolate chips until fully melted and homogenous.
05 - Pour the pudding into individual serving dishes and cover each surface directly with plastic wrap to prevent a skin from forming.
06 - Refrigerate for a minimum of 2 hours to allow the pudding to set.
07 - In a chilled mixing bowl, beat heavy whipping cream, powdered sugar, and vanilla extract with a hand mixer or whisk until soft peaks form.
08 - Top each set pudding portion with a generous dollop of whipped cream and serve immediately.