Preheat your oven to 350°F (175°C). Grease and lightly flour a 9" x 13" baking pan.
In a large mixing bowl, sift together the flour, cocoa powder, sugar, baking powder, baking soda, and salt until well combined.
Make a well in the center of the dry ingredients. Add the egg, milk, vegetable oil, and vanilla extract. Mix until just combined. The batter might seem thick at this point.
Slowly incorporate the boiling water into the batter, mixing continuously until smooth. The batter will thin out.
Transfer the batter to the prepared baking pan, spreading it out evenly. Tap the pan lightly on the countertop to remove any air bubbles.
Place it in the preheated oven and bake for 25-30 minutes, or until a toothpick inserted into the center comes out clean or with just a few crumbs attached.
For the cake pops:
Once the cake is removed from the oven, carefully add the baked cake into the bowl of a stand mixer. You can break it into pieces or chunks to move it into the mixer. Use the paddle attachment to mix the hot cake on medium speed until a dough forms.
Melt the orange candy melts and coconut oil in a microwave safe bowl. Heat for 30 second and stir – repeating until the candy is melted and smooth.
Use a sharp knife to cut a small slit in each silicone pumpkin mold, large enough for the popsicle sticks.
Spread a layer of the melted orange candy coating to the molds, making sure to coat the sides well. Slide the popsicle sticks in and let them chill in the freezer for about ten minutes.
Add the cake pop dough to the molds,
Then top with another layer of candy coating on the back of the pumpkins. Chill again for ten minutes.
Carefully pull the sides of the silicon mold outward to release the cake pop, carefully pulling the stick through the slit.
If your cake pops are not fully coated in the candy coating, you can add additional orange coating to the exposed areas with a knife.
Use black frosting to fill in the jack-o-lantern eyes, nose and mouth (or leave them orange if you prefer). Let the cake pops set until they are hardened and enjoy!