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Pre-heat oven to 350 degrees F (180 C) and line a baking tray with parchment or silicone baking pads. Beat shortening and sugar until creamy, then add applesauce and coconut milk. Mix in all other ingredients ending with flour until completely mixed.
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Combine sugar and cinnamon in a small bowl then divide half into another small bowl so you have one for rolling dough in and one for sprinkling on top of chocolate.
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Take some wine corks and wrap them in one sheet of foil and press down to smooth as much as possible to the shape. Grease the inside of 12 to 14 (or as many as you have and bake in 2 batches) tall juice glasses (or pop-over pans.) If you can't reach bottom of glasses use a greased napkin and a butter knife to get to the bottom.
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Roll the dough into 3 tablespoon sized balls, dip in cinnamon/sugar mixture to coat all sides, and flatten into disc shapes. Take as many corks as you have wrapped in foil and stand them up in the center of dough discs (see picture). Wrap around cork and shape into a cup as best as you can, then drop into your greased glasses. Place the glasses on a baking tray and space about 1 inch apart.
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Bake for 9 - 11 minutes or until the sides or edges start to darken slightly. Remove and allow them to cool for at least 5 minutes then loosen edges with a slim knife and invert cups to carefully shake them out. Remove corks gently. Just know you'll likely have at least one fail.
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Melt the chocolate in a double boiler and spread a thin layer onto the inside of the cookie cups (do your best to get any hole or the cookies will leak.) Spread it up on the rim and dip rims in cinnamon and sugar. Place finished cups in fridge until chocolate has hardened then feel free to pour in your ice cold milk and devour!