01 - In a medium saucepan, whisk together sugar, cocoa powder, cornstarch, and salt.
02 - Gradually whisk in the milk until the mixture is smooth and free of lumps.
03 - Place the saucepan over medium heat. Cook, whisking constantly, until the mixture begins to thicken and comes to a gentle boil, about 5–7 minutes.
04 - Once thickened, remove the saucepan from the heat. Stir in the vanilla extract and chocolate chips until smooth and fully melted.
05 - Pour the pudding into individual serving dishes. Cover each with plastic wrap, pressing it directly onto the pudding surface to prevent skin from forming.
06 - Chill in the refrigerator for at least 2 hours, or until set.
07 - In a cold mixing bowl, beat heavy cream, powdered sugar, and vanilla extract with a hand mixer or whisk until soft peaks form.
08 - Once the pudding is set, top each serving with a generous dollop of whipped cream. Serve immediately.