Add coconut milk to a medium, heavy-bottomed saucepan set to medium heat. Add the maple syrup, cocoa powder, coconut sugar, and salt, whisking everything together well as the mixture heats.
Remove the saucepan from the burner and immediately add chopped dark chocolate. Stir it in until completely smooth, and then stir in the vanilla extract.
Carefully divide the hot pudding between four to six small serving jars or ramekins. To prevent a skin from forming, cover the surface of each directly with plastic wrap.
Open two cans of coconut milk and scoop the cream into a cold mixing bowl. Add powdered sugar and vanilla extract and whip with a handheld electric mixer on medium speed until the mixture is fluffy.