Preheat your oven to 350°F (175°C). Lightly grease a 9x13 inch baking pan and line it with parchment paper. Set aside.

In a large mixing bowl, combine the white cake mix, 1 can of cherry pie filling, lightly beaten eggs, vegetable oil, and pure vanilla extract. Mix until thoroughly combined.

Pour the cake batter into the prepared pan and bake for 35 to 40 minutes, or until a toothpick inserted into the center comes out clean. Allow the cake to cool completely before frosting.

In a microwave-safe bowl, combine the semisweet chocolate chips, evaporated milk, butter, and vanilla extract. Microwave for 30 seconds, then remove and whisk until the mixture is smooth.

Add the powdered sugar to the chocolate mixture and continue whisking until the frosting is smooth and well combined.

Spread the frosting evenly over the cooled cake. Top the frosted cake with the remaining can of cherry pie filling. Serve and enjoy!