Make the pudding: Whisk the egg yolks, sugar and cornstarch in a large bowl.
Combine the milk, chocolate and salt in a saucepan over medium heat and stir until the chocolate melts. Gradually pour the hot chocolate mixture into the egg mixture, whisking constantly. Pour back into the saucepan and stir until thick, 12 to 15 minutes. Remove from the heat and stir in the vanilla, then divide among 6 to 8 dessert cups or dishes. Cover with plastic wrap and refrigerate until set, about 2 hours.
Meanwhile, make the cinnamon cream: Whip the cream with the sugar in a bowl until it just holds soft peaks; fold in the cinnamon. Serve with the pudding.