Place bittersweet chocolate into a medium bowl and set aside.
Using a medium sized pan over medium heat, ad coco powder, heavy cream, and cold milk. Heat to simmer.
Pour milk mixture over bittersweet chocolate. Let sit for 2-3 minutes.
Whisk gently to combine, then add vanilla and continue whisking till thouroughly mixed.
Pour into popsicle molds and freeze for a minimum of 4 hours. NOTE: A turkey baster will do the trick nicely for filling the molds or you can use a container with a spout, such as a large measuring cup.