Preheat your oven to 350°F (175°C). Grease and flour two 8-inch round cake pans.
In a large bowl, whisk together the dry cake mix and instant espresso powder. Add the water, oil, eggs, and 1 1/2 teaspoons of orange extract. Mix according to package directions, scraping the bowl as needed, until just combined.
Pour the batter evenly into the two prepared pans. Bake for 28-32 minutes, or until a wooden skewer inserted into the center of the cakes comes out clean.
Let the cakes cool in their pans on a wire rack for 10 minutes. Then, carefully invert them onto the rack to cool completely.
While the cakes cool, make the ganache. Place the chopped chocolate in a medium heatproof bowl. Heat the heavy cream in a small saucepan over medium heat until it just begins to simmer. Pour the hot cream over the chocolate and let it stand for 5 minutes without stirring. Add the 1/2 teaspoon of orange extract, then stir gently until the ganache is smooth and glossy. Set aside to cool and thicken.
To make the frosting, beat the softened butter in a large bowl with an electric mixer until creamy. Sift in the powdered sugar and cocoa powder. Add the milk and vanilla extract. Beat on low speed until combined, then increase to medium-high and beat for 3 minutes until light and fluffy.
To assemble, place one cooled cake layer on a serving plate or cake stand. Spread the thickened ganache evenly over the top, right to the edge. Place the second cake layer on top.
Frost the top and sides of the cake with the chocolate frosting. For a cleaner look, you can apply a thin 'crumb coat' of frosting, chill the cake for 20 minutes, then apply the final layer.