Step 1

Place 20 ounces frozen sweet dark cherries for the filling in a medium saucepan and let sit at room temperature to start thawing while making the cake batter.

Step 2

Place 1 cup whole milk and 1/2 cup sour cream in a medium bowl and whisk to combine. Place 3 large eggs on the counter. Let everything sit until room temperature.

Step 3

Arrange a rack in the middle of the oven and heat the oven to 350ºF. Coat 3 (9-inch) round cake pans with cooking spray, then line the bottom of each with a parchment paper round.

Step 4

Place 2 1/2 cups all-purpose flour, 1 cup natural cocoa powder, 2 1/2 teaspoons baking soda, and 1 1/4 teaspoons baking powder in a medium bowl and whisk to combine.

Step 5

Place the eggs, 2 1/2 cups granulated sugar, 1 cup vegetable oil, 2 teaspoons vanilla extract, and 1 1/4 teaspoons kosher salt in the bowl of a stand mixer (or large bowl if using an electric hand mixer). Beat with the paddle attachment on medium-low speed until smooth, about 1 minute.

Step 6

Add the flour mixture and beat on low speed until just combined. With the mixer on low speed, pour in 1 cup hot brewed coffee. Add the milk and sour cream mixture and beat until just combined. Scrape down the sides and bottom of the bowl with a flexible spatula. Beat on medium speed until smooth, about 1 minute (the batter will be thin). Divide the batter between the cake pans (about 22 ounces each).

Step 7

Bake, rotating the pans halfway through, until the top of the cakes bounces back when gently pressed and a toothpick comes out clean, 35 to 40 minutes total. Meanwhile, make the cherry filling and chocolate shavings.

Step 8

Place on a wire rack for 15 minutes. Flip the cakes out onto the racks and discard the parchment. Let cool completely, at least 1 hour.

Step 9

Reserve 1 cup of the cherries. Add 1/3 cup granulated sugar to the saucepan with the remaining cherries and toss to combine. Cook over medium-low heat until the cherries become saucy, about 3 minutes. Lightly crush the cherries with a potato masher and continue to cook until the sauce comes to a simmer, about 5 minutes.

Step 10

Place 3 tablespoons cornstarch and 3 tablespoons water in a small bowl, and whisk until the cornstarch is suspended. Pour into the saucepan and cook, stirring constantly, until the sauce is thickened and no longer tastes starchy, 2 to 3 minutes.

Step 11

Turn off the heat. Add the reserved cherries, 1 teaspoon of the kirsch if using, and 1/2 teaspoon almond extract, and stir to combine. Taste and add 1 more teaspoon kirsch if desired.

Step 12

Transfer to a shallow bowl. Press a sheet of plastic wrap directly onto the surface of the filling. Refrigerate until completely chilled and set, about 2 hours. Meanwhile, make the chocolate shavings.

Step 13

Coarsely chop 3 1/2 ounces semisweet chocolate and place in a medium microwave-safe bowl (no need to chop if using chocolate chips). Microwave, stirring every 20 seconds, until melted and smooth. Spread the chocolate onto a piece of parchment paper into a thin, roughly 10-inch square. Gently roll up the parchment into a loose spiral about 2 inches wide, so that the chocolate is contained inside. Refrigerate until the chocolate is set, at least 15 minutes.

Step 14

Unroll the parchment, breaking the chocolate into long pieces in the process. If there are any especially large or wide pieces, break them up by hand. Refrigerate until ready to use.

Step 15

When ready to assemble the cake, place 1 quart cold heavy cream, 2/3 cup powdered sugar, 2 tablespoons dried milk powder if using, and 1 1/2 teaspoons vanilla extract in the clean, dry bowl of a stand mixer (or large bowl if you are using an electric hand mixer). Beat with the whisk attachment on medium-high speed until stiff peaks form, 3 to 4 minutes.

Step 16

Transfer 1 1/4 cups to a piping bag with the tip snipped off (or a large zip top bag) and 3/4 cup to a piping bag fitted with a large fluted tip.

Step 17

Place 12 maraschino cherries on a paper towel-lined plate to absorb the excess syrup.

Step 18

If there is any doming on the cake layers, trim it off with a long serrated knife so the cakes are completely flat.

Step 19

Spread about 1 tablespoon of the whipped cream in the center of a cake or serving plate. Top with 1 cake layer. Pipe a border of whipped cream (from the bigger piping bag) around the edges of the cake. Dollop half of the filling (about 1 heaping cup) onto the cake and spread into an even layer, going all the way to the whipped cream border. Spread 2/3 cup of the whipped cream over the cherry filling.

Step 20

Top with the second cake layer. Repeat piping a whipped cream border, layering with the remaining cherry filling, and spreading 2/3 cup of the whipped cream on top. Top with the final cake layer.

Step 21

Frost the top and sides with the remaining whipped cream and smooth out. Use an offset spatula or butter knife to gently swipe angled lines upward along the sides of the cake, to give an evenly patterned texture. Use the piping bag with the fitted tip, pipe 12 rosettes evenly around the top edges of the cake.

Step 22

Fill the center of the cake with the largest chocolate shavings, piling them up to give height. Press the smaller pieces of chocolate around the bottom edge of the cake, breaking some pieces up as needed.

Step 23

Place a maraschino cherry on top of each whipped cream rosette. Refrigerate the cake for at least 30 minutes or up to 1 day before slicing and serving.