Gather all ingredients.

Preheat the oven to 350°F (175°C). Grease and flour two 9-inch round cake pans; line bottoms with parchment paper.

Place a medium bowl in the refrigerator to chill before using it to whip the cream.

Whisk flour, sugar, cocoa, baking powder, baking soda, and salt together in a large bowl.

Add eggs, milk, oil, and vanilla; beat until combined.

Pour cake batter into the prepared pans.

Bake in the preheated oven until a toothpick inserted in the centers comes out clean, about 35 minutes.

Cool layers in pans on wire racks for 10 minutes. Run a paring knife around edges to loosen and invert carefully onto racks to cool completely, about 1-2 hours.

While cake layers bake, drain cherries for topping, reserving 1/2 cup juice. Combine reserved juice, cherries, sugar, and cornstarch in a saucepan.

Cook over low heat, stirring constantly, until thickened. Let cool at room temperature for 30 minutes, then transfer to the refrigerator until chilled.

To make the frosting, combine whipping cream and confectioners' sugar in the chilled bowl. Beat with an electric mixer at high speed until stiff peaks form.

Split each cooled cake layer in half horizontally using a long serrated knife and tear one layer into crumbs; set aside.

To assemble, place one layer on a plate. Spread with 1 cup frosting and 3/4 cup cherry filling. Repeat for second and third layers. Frost sides of the cake with remaining frosting.

Pat reserved cake crumbs onto sides of the cake. Use 1½ cups frosting in a piping bag with a star tip to decorate edges and top.