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Preheat the oven to 350°F with a rack in the center. Grease a 9" x 13" pan with nonstick spray, then line it with a parchment sling and lightly grease the parchment.
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To make the cake: In the bowl of a stand mixer fitted with the flat beater attachment (or in a large bowl with a hand mixer), combine the eggs and granulated sugar. Beat on medium-high speed until frothy and light, about 2 minutes. Add the cocoa and beat for another 1 minute. Add the oil, water, and vanilla and mix on medium-low to combine.
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In a medium bowl, whisk together the flour, baking soda, and salt. With the mixer running on medium speed, slowly add about one-third of the flour mixture to the chocolate mixture, followed by half of the buttermilk. While the mixer is running, add half of the remaining flour mixture, the remaining buttermilk and, finally, the remaining flour mixture. Stop the mixer and use a flexible spatula to scrape the bottom and the sides of the bowl, then beat on medium for 30 seconds more. Pour the batter into the prepared pan.
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Bake for 30 to 33 minutes, until the top springs back when lightly pressed and the edges just begin to pull away from the pan. Remove from the oven and set on a wire rack. Let the cake cool completely in the pan.
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To make the cherry buttercream: In the bowl of a stand mixer fitted with the flat beater attachment (or in a large bowl with a hand mixer), beat the butter on medium-high speed until fluffy. Beat in the salt. With the mixer on low, gradually add the confectioners' sugar (if you add too much at once it will poof up in your face!).
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Once all the confectioners’ sugar has been added, increase the mixer speed to medium-high and beat until smooth (it will be very dry and not look like frosting — yet!). Stop the mixer and use a flexible spatula to scrape the sides and bottom of the bowl. Add the cherry concentrate, 1 tablespoon at a time (but use no more than 4 tablespoons or 84g) and beat between each addition until the frosting is deeply colored and flavored. If necessary to thin to a spreadable consistency, add the half-and-half or milk.
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Use an offset or flexible spatula to spread the cherry buttercream onto the cooled cake in an even, thin layer.
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To make the chocolate topping: In a small saucepan, heat the half-and-half over medium heat until little bubbles appear at the edges of the pan. Remove from the heat and add the chocolate. Let sit for 5 minutes, then stir until smooth.
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Pour the warm ganache in puddles all over the cherry buttercream and carefully smooth it out with an offset spatula or flexible spatula so that it fully covers the surface. Freeze the cake until the chocolate layer is set, about 15 minutes.
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Remove the cake from the freezer and use a warm knife to cut the cake into squares, dipping the knife into warm water and wiping it dry with a towel between cuts so you get nice, neat pieces. Garnish each piece with a cherry and serve with whipped cream, if desired.
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Storage information: Store leftover Chocolate-Covered Cherry Cake, covered and refrigerated, for up to 3 days.