Preheat oven to 350°. Spray a 13×9-inch baking pan with baking spray with flour.

In a large bowl, whisk together buttermilk, oil, eggs, and 2 teaspoons vanilla until combined.

In a medium bowl, whisk together flour, granulated sugar, cocoa, brown sugar, baking powder, baking soda, and salt. Gradually whisk flour mixture into buttermilk mixture just until combined. Whisk in ¾ cup hot water. (Batter will be thin.) Pour batter into prepared pan.

Bake until a wooden pick inserted in center comes out clean, 30 to 35 minutes. Let cool completely in pan on a wire rack.

Using a serrated knife, trim ½ inch off sides of cake, discarding scraps. Cut cake into 1-inch pieces.

In a medium bowl, stir together pie filling, orange zest and juice, and almond extract. In a large bowl, beat cold cream, confectioners’ sugar, and remaining ½ teaspoon vanilla with a mixer at medium-high speed until soft to medium peaks form.

Place a layer of cake pieces in bottom of a 3-quart trifle dish. Spread 1½ cups whipped cream onto cake; top with 1 cup cherry mixture. Repeat layers twice. Loosely cover, and refrigerate for at least 2 hours before serving or up to 2 days.