Preheat oven to 350 degrees F. Line 24-muffin cups with cupcake liners or spray with with baking spray.
Sift together dry ingredients: flour, cocoa powder, baking powder, baking soda, salt, cinnamon, pumpkin pie spice, and espresso powder. Set aside.
In a medium bowl, whisk together buttermilk, sour cream, pumpkin puree and vanilla. Set aside.
Using a stand mixer, cream together butter and sugars with paddle attachment. Add eggs one at a time, making sure to scrape down bowl between eggs.
In three additions, alternate adding dry mixture and wet mixture to butter. Scrape down bowl as needed to make sure all ingredients are fully incorporated.
Using a large cookie scoop, divide the batter between 24 cupcake cups. Bake for 16-20 minutes until toothpick inserted in the center comes out clean. Let cupcakes rest for a couple minutes and remove from pan to cool completely.
Orange Marshmallow Filling:
In the bowl of a stand mixer, beat the cream cheese until light and fluffy.
Add the marshmallow fluff and beat on medium until smooth.
Add the orange and vanilla extract and the pinch of salt. Mix on medium until incorporated.
Reduce speed to low. Add in confectioners sugar and beat until smooth.
In a separate, clean metal bowl, whip heavy cream until stiff peaks form.
Gently fold whipped cream into marshmallow mixture.
Place in the fridge for about 20 minutes, or so for it to firm up a bit.
Chocolate Ganache
Place chocolate in a medium heat-proof bowl. (Do not use plastic.)
Heat the cream in a small saucepan over medium heat until it begins to gently simmer. (Do not let it come to a boil. It will make a giant mess on your stove and salad your chocolate).
Pour over the chocolate, and let it sit for 2-3 minutes to gently soften the chocolate.
With a metal spoon or small rubber spatula, very slowly stir until completely combined and chocolate has melted. Allow to cool on the counter for about 30 minutes before drizzling over the cake.
Orange Buttercream Frosting
In the bowl of a stand mixer, beat the butter until light and fluffy.
Add pinch of salt, confectioners sugar, and extracts until well combined and creamy.
Add orange juice and beat until creamy. Add additional confectioners sugar or heavy cream until correct piping consistency.
To Assemble the Cupcakes
Add filling to a pastry bag fitted with a round top. Push the tip into the top center of the cake and squeeze. Continue adding filling until you see the filing burst through the top of the cake.
Frost the cupcakes with orange buttercream frosting. I like to use a pastry bag fitted with a large star tip for a pretty swirl.
Drizzle chocolate ganache on top of frosting. Sprinkle with Halloween decorations of desired.
Frosting Notes:You want a firm frosting so you can pipe it into your cupcakes. You may need to add little bit more confectioners sugar to thicken it up. If the frosting is too firm, add heavy cream one tablespoon at a time to make it creamier. Do not add more orange juice or your frosting will get grainy.Ganache Notes:If your chocolate is not melting, do not microwave it. Transfer it to the top of a double boiler or place the bowl over the pot. You only want about an inch of simmering water in the pot. The bottom of the bowl should not touch the water.For best results, allow ganache to cool at room temperature. It will thicken as it cools. Refrigerating speeds this up, but the ganache will not cool evenly. Be sure to stir it a few times if you place it in the refrigerator to set so that it remains even and smooth.Once completely cool and thick, the ganache can be piped with a piping tip or scooped with a spoon. You can also beat the cooled thickened ganache with a handheld or stand mixer fitted with a whisk attachment until light in color and texture, about 4 minutes on medium-high speed.Cooled ganache can be stores in the fridge for up to five days. Cover tightly and store. To rewarm or thin out again, stir constantly over low heat on the stove in either (1) a double boiler or (2) in a heatproof bowl placed over a pot of simmering water. Don’t let the bottom of the bowl touch the simmering water.Once ganache cools completely, you can cover it tightly and freeze it for up to 3 months. Thaw in the refrigerator before use.Ganache will only set if the correct chocolate is used. You can use high quality chocolate chips if needed (I prefer Vermont Nut Free or Enjoy Life semi-sweet chocolate chips), but I recommend using pure chocolate baking bars. You can find them in the baking aisle. They are sold in 4 ounce bars. Bakers' Bars are nut free (but always check the labels)