Dark as night and deeply chocolate, these Glazed, Filled, Sugared, & Dipped chocolate cake doughnuts are bittersweet and coated in a milky sugar glaze.
In the bowl of a stand mixer fitted with the paddle attachment, mix 1 cup of the flour, the cocoa powder, sugar, baking powder, baking soda, cinnamon, and salt. Add the eggs and yolks and mix well. Add the buttermilk, vanilla, and oil, and mix until combined. Add the remaining 2 cups flour and mix until just barely combined.
Scrape the dough onto a sheet of parchment paper and put another sheet of parchment paper on top. Using a rolling pin, flatten and roll the dough until it's 3/8 to 1/2 inch thick. Put the dough in the refrigerator and chill for 30 minutes to 1 hour, until it no longer clings when you try to lift it off the parchment paper.
Heat at least 2 inches of oil in a heavy-bottomed pot fitted with a deep-fry thermometer until the oil reaches 350°F. Prepare two baking sheets: one lined with paper towels, and the other dusted with flour.
Peel off the top sheet of parchment paper and flip the dough onto a floured work surface. Remove the second sheet of parchment paper and dust the dough with flour. Using a floured biscuit or doughnut cutter, cut the dough into 2 1/2- to 3-inch tubular rounds and put them on the flour-dusted baking sheet.
Fry the doughnuts in batches, taking care not to crowd the pot, until slightly red-brown all over, 1 to 2 minutes per side. Drain on the paper-towel-lined baking sheet.
Whisk the milk and powdered sugar together in a bowl. While the doughnuts are still warm, dip them one at a time in the glaze, flipping once so that the entire doughnut is coated in glaze. Put them on a wire rack to set.
Once dry, serve them immediately, or store at room temperature for up to 2 days.
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