Pre-heat the oven to 425 degrees. Get out two 9 inch cake pans, line them with parchment paper on the bottom and spray them liberally with cooking spray. In a large mixing bowl, whisk the flour, 1/2 cup sugar, cocoa powder, baking powder, and salt together to aerate them. Add in the butter and cut it into the dry ingredients with a pastry blender without over working it. It should look pebbly. In a separate bowl, whisk together the eggs and milk. Pour it into the rest of the ingredients and gently mix it in. Bring the dough together with your hands and knead it for about a minute in the bowl. Divide the dough in half and gently press each half out to evenly fill each cake pan. Bake the chocolate strawberry shortcake for 15 minutes.

While the cake bakes, stir the chopped strawberries with the extra 1/3 cup sugar in a bowl. Set it aside, then prepare the whipped cream. Pour the heavy whipping cream into a bowl and whip it with a hand mixer until it becomes fluffy and holds it shape. Add in the powdered sugar and vanilla and whip it all together more with the hand mixer just until it has stiff peaks. The cakes should be done by this point. Take them out and let them cool for 20 minutes. Then turn them out onto a clean cutting board to finish cooling.

Time to assemble the cake! Place one of the cake layers onto a cake plate and spread a generous layer of whipped cream onto it. Then evenly distribute the strawberries on top of the whipped cream. Put the second layer of cake on top of that and gently press down so that it all holds together without squishing the filling out. Spread another very generous layer of whipped cream on top and garnish the top with the 3 additional strawberries. You may not need all of the whipped cream, store any leftovers for ice cream sundaes! Slice and serve it to the delight of your guests. Enjoy!