Preheat the oven to 350°F (175°C). Grease and flour the two 9-inch round cake pans and line the bottom with parchment paper.
In a large mixing bowl, combine the flour, sugar, cocoa powder, baking powder, baking soda, and salt. Mix until well combined.
Add the eggs, milk, vegetable oil, and vanilla extract to the dry ingredients. Beat on medium speed for about 2 minutes until smooth.
Carefully stir in the boiling water until well combined; the batter will be thin.
Divide the batter evenly between the prepared pans.
Bake for 30 minutes, or until a toothpick inserted in the center comes out clean.
Allow the cakes to cool in the pans for 10 minutes, then transfer to a cooling rack to cool completely.
While the cakes are cooling, prepare the raspberry filling by mashing the fresh raspberries in a bowl until slightly pureed.
For the ganache, heat the heavy cream in a saucepan over medium heat until just boiling. Remove from heat and add the chopped chocolate. Stir until smooth and glossy. Let it cool slightly to thicken.
Once the cakes are completely cooled, place one layer on a serving plate. Spread the mashed raspberries on top and then carefully place the second layer on top.
Pour the chocolate ganache over the top of the cake, allowing it to drip down the sides.
Chill the cake in the refrigerator for about 30 minutes to set the ganache before serving.