Melt 2 cups of chocolate in a double boiler until smooth.
Use a silicone muffin tray or silicone liners OR line a muffin tin with paper liners. Use a brush or a spoon to spread about ½ – 1 tablespoon of melted chocolate in the bottom of each liner and up onto the sides to create a cup. Place in freezer for about 10 minutes to harden.
While the chocolate hardens, pulse together the cashew butter, pumpkin puree, tapioca and almond flour, maple syrup, pumpkin pie spice, vanilla extract and salt in a food processor until well combine. Then fold in the chocolate chips.
Once chocolate is hard, use a cookie scoop to scoop 1 tablespoon of pumpkin pie cookie dough into the middle of the chocolate cup, flattening it out on top and keeping room around the sides so the chocolate cup can be sealed. Repeat with all the chocolate cups then place back in the freezer for 10 minutes to help harden the cookie dough.
After ten minutes, pour the rest of the chocolate on top of each chocolate cup, sealing up the sides and covering the top. Sprinkle with coarse sea salt on top then place in the fridge for 10 minutes before eating them up!