Sprinkle the gelatin over the top of the remaining ¼ cup of milk still in the measuring cup. Let it sit to bloom.
Meanwhile, heat the milk in the saucepan over medium heat and add the chocolate chips. Using a flat whisk (I use this flat whisk), stir the chocolate chips until they begin to melt.
When the chips are melting, whisk well until they’re completely dissolved and then immediately remove the milk from the heat.
Whisk in the vanilla extract.
Stir the measuring cup with the bloomed gelatin so it’s mixed well. While whisking continuously, pour the gelatin mixture into the chocolate milk. Whisk well.
Pour evenly between four 4 oz mason jars. Place a piece of plastic wrap over the surface of the mixture to prevent a thick film from forming. This doesn’t have to be perfect, but do your best to avoid any significant air pockets.
Place in the refrigerator and let it set for 2 hours. At that point you can serve or keep it for later.
When you serve, remove the plastic wrap and top with homemade whipped cream, homemade chocolate whipped cream, fresh fruit and/or just eat plain.
To keep for later, place the mason jar lids on the jars with the plastic still cover the pudding.