Preheat your oven to 350°F (175°C). Grease and line a 15x10-inch jelly roll pan with parchment paper, allowing some overhang for easy removal later.
In a large mixing bowl, whisk together the flour, granulated sugar, cocoa powder, baking powder, baking soda, and salt until well combined.
In another bowl, beat the eggs, milk, vegetable oil, and 2 teaspoons of vanilla extract until smooth. Gradually add the wet ingredients to the dry ingredients, mixing until just combined.
Pour the batter into the prepared pan, spreading it evenly. Bake for 12-15 minutes, or until a toothpick inserted in the center comes out clean.
While the cake is baking, prepare a clean kitchen towel by dusting it with powdered sugar. Once the cake is done, remove it from the oven and immediately invert it onto the prepared towel. Carefully peel off the parchment paper.
Starting from one short end, roll the cake up tightly in the towel. Let it cool completely in this rolled position, about 30-45 minutes.
Once cooled, unroll the cake gently. Spread the cherry pie filling evenly over the surface, leaving a small border around the edges.
In a separate bowl, whip the heavy cream with the powdered sugar and 1 teaspoon of vanilla extract until stiff peaks form. Spread the whipped cream over the cherry filling.
Roll the cake back up carefully without the towel. Place seam-side down on a serving platter.
Garnish with chocolate shavings if desired. Slice and serve chilled or at room temperature.