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Grab your KitchenAid Standing Mixer and whip together the heavy whipping cream on medium-high speed. When the cream starts to come together, add in your sweetened condensed milk and vanilla. Keep whipping until well combined.
Using your rubber spatula, transfer contents from KitchenAid mixing bowl to your freezer safe container. Fill about half of the container, then layer with blueberries. Add another layer of ice cream mixture and top off with a final layer of blueberries. Cover and let sit in the freezer for at least 4 hours. If you want the ice cream to be firmer, leave for 6 hours.
Add your cocoa powder to your KitchenAid mixer after the vanilla extract. Whip until well combined and contents turn brown. If you want more of a chocolate taste, add 1 tablespoon of cocoa powder at a time and taste test to your liking. Then transfer contents to freezer safe container, cover, and let sit in the freezer.