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For the cupcakes:
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Preheat oven to 350u00b0F. Line two standard 12 cup muffin tins with paper liners.
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Mix together sugar, flour, cocoa, baking powder, baking soda and salt in the bowl of a stand mixer or any large bowl. Add eggs, milk, oil and vanilla. Beat on medium speed either with a stand mixer or a hand mixer for 2 minutes. Turn off mixer. Stir in boiling water and incorporate with all ingredients with a large spoon or ladle (batter will be thin).
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Divide batter evenly among lined muffin cups, filling each about 2/3 of the way.
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Bake for 20-25 minutes, until a toothpick inserted in the center comes out clean. Remove from oven. Allow to cool completely before filling and frosting.
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For the filling:
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In the bowl of a stand mixer, beat butter and sugar on low-medium speed. Once blended, add Marshmallow Fluff and cream and increase the speed to medium-high. Beat for an additional 1 to 2 minutes, or until light and fluffy.
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Transfer the filling to a pastry bag fitted with a round 1/4-inch tip, and fill bag with all but 1/4 cup of the filling. Put the extra 1/4 cup in a pastry bag fitted with a smaller round tip or a zip-lock with a tiny corner snipped and keep aside.
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For the ganache icing:
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Pour the cream into a glass bowl. Bring to a boil in the microwave by cooking for 1 minute increments until it begins to bubble. Don't let it boil over.
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Remove the hot cream from the microwave. Add the chocolate and butter and cover bowl with plastic wrap. Let it stand for 1 minute, then open and stir with a spatula until chocolate is melted and smooth. If not, place it back in the microwave and heat on 50% power for 20 seconds intervals until blended and completely smooth. Set aside to cool and thicken for 10-15 minutes.
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For the assembly:
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Take the cupcakes, plunge the tip end of the larger filled pastry bag into the top center of the cupcake. Press and fill roughly about 2 tablespoons full or just until you feel the cupcake swell. Repeat with remaining cupcakes.
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Dip the top of each filled cupcake into ganache, flip and set aside. Repeat with remaining cupcakes. Allow icing to set, about 20 minutes.
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Take the smaller pastry bag/zip-lock bag of filling and pipe a continuing squiggle across the top middle of each cupcake.
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Place any remaining cupcakes in an airtight container and store in the refrigerator.
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Cake recipe adapted from Hershey's Perfectly Chocolate-Chocolate Cake; filling adapted from foodandwine.com.
