In a large bowl, whisk together the flour, sugar, cocoa powder, baking soda, baking powder, and salt. Make sure to break up any cocoa powder lumps – they can be sneaky and leave bitter spots in your cupcakes.

Brew your coffee and keep it hot – this is important because hot coffee helps bloom the cocoa powder, making the chocolate flavor deeper and richer.

In a separate bowl, whisk together the eggs, milk, oil, and vanilla until well combined. The mixture should be smooth and uniform in color.

Pour the wet ingredients into the dry ingredients. Start mixing with a whisk or spatula until mostly combined – you’ll still see some flour streaks and that’s okay.

Add the hot coffee and mix until the batter is smooth. It will be quite thin, almost like chocolate soup – don’t worry, that’s exactly what you want!

Fill each cupcake liner about 2/3 full (about 3 tablespoons of batter). I use an ice cream scoop to make this easier and keep them uniform.

Bake for 18-20 minutes. You’ll know they’re done when a toothpick inserted in the center comes out clean and the tops spring back when lightly pressed. The surface should look set and no longer shiny.

Let them cool in the pans for about 5 minutes (they’re fragile when hot), then transfer to a wire rack to cool completely before frosting.

Start with your butter at room temperature – it should be soft enough that your finger leaves an indent when pressed, but not so soft it’s greasy or melting.

Add the pumpkin puree, vanilla, pumpkin pie spice, and salt. Beat until well combined. The mixture might look a bit curdled at this point – don’t panic, it’ll come together!

Gradually add the powdered sugar, about 1 cup at a time, beating well after each addition. Scrape down the sides of the bowl frequently. The frosting will start to thicken and become more orange in color.

Beat on medium-high speed for 3-4 minutes until light and fluffy. If the frosting seems too thick, add heavy cream one tablespoon at a time until you reach a pipeable consistency. It should hold its shape but be soft enough to pipe smoothly.