Soak corn husks. Bring a large pot of water to a boil. Remove from heat and soak the corn husks, pushing them under water with kitchen tongs. Let soak 30 minutes then remove from the water and wipe clean. You will need 24 corn husks that are at least 4-5 inches wide at the bottom. 

Combine dry ingredients. Meanwhile, combine masa harina, cocoa powder, cinnamon, baking powder, salt, and chipotle powder in a large bowl. Whisk until completely incorporated. 

Beat butter. Combine butter or coconut oil and sugar in the bowl of a stand mixer fitted with the paddle attachment. Beat on medium until very fluffy, about 3-4 minutes. Don't skimp on this step, this is what gives you fluffy tamales. 

Mix wet ingredients. Combine milk and vanilla in a liquid measuring cup. 

Make the masa. Scrape down the sides of the mixing bowl then add 1/3 of the masa mixture. Mix on low until combined. Add half of the milk, mix to combine, then repeat until all the masa and milk mixtures have been added, scraping down the sides of the bowl as you go. 

Add chocolate. Add chocolate chips and mix on low just until combined. 

Fill corn husks. Scoop 1/4-1/3 cup of the chocolate masa and roll into a 3-4 inch log with your hands. Place the corn husk on a clean surface with the wide side closest to you. Place the masa log on one side of the corn husk and roll the corn husk around the log, covering completely. Fold the skinny top half over the bottom half and place seam-side down on a baking sheet. Repeat with remaining corn husks and dough. 

Prepare tamales steamer. Fill the bottom of a tamales steamer with water then place the steamer rack on top. You can also use a pasta pot that has a removable liner or a large stock pot with a steaming basket. Place over high heat. 

Steam tamales. Once pot is filled with steam, carefully stand the tamales, open-side-up, in the pot so they are leaning on each other and don't fall over and unravel. Cover tightly and steam for 45 minutes or until the dough is firm and cooked through. Check the water level occasionally to make sure the pot doesn't dry out. 

Serve! Serve warm with cinnamon sugar and spicy honey. Enjoy!