Preheat the oven to 350°F. Line a 12 cup muffin pan with paper liners and set aside.
In a small bowl whisk together the flour, cocoa powder, baking powder, baking soda, salt, and espresso powder until well combined.
In a large bowl add 1/4 cup softened butter and the granulated sugar. Beat with an electric mixer on medium high speed for 1 to 2 minutes until pale and fluffy.
Add the egg, egg yolk, and 1 teaspoon vanilla to the butter mixture. Beat on medium speed for 1 to 2 minutes until light and well combined.
Add the milk and sour cream to the bowl and mix on low speed until just combined; the mixture may look slightly curdled.
Add the dry ingredients to the wet ingredients and mix on low speed until just combined and no dry streaks remain; do not overmix.
Divide the batter evenly among the 12 liners, filling each about three quarters full.
Bake for 17 to 20 minutes, until the tops spring back when lightly touched and a toothpick inserted in the centers comes out clean or with a few moist crumbs.
Let the cupcakes cool in the pan for 10 minutes, then transfer them to a wire rack to cool completely.
While the cupcakes cool, heat the heavy cream in a small saucepan over medium heat until steaming and just starting to simmer at the edges.
Place the chopped semi-sweet chocolate in a medium heatproof bowl, then pour the hot cream over the chocolate and let stand for 2 minutes.
Stir the chocolate and cream together until smooth and glossy, then stir in 1/4 cup raspberry preserves until fully combined. Let the ganache cool for 15 minutes until thickened but still spoonable, then transfer to a piping bag if desired.
When the cupcakes are completely cool, use a small paring knife or cupcake corer to cut a shallow cone from the center of each cupcake.
Spoon or pipe some raspberry chocolate ganache into the center of each cupcake, then trim the point off each removed cone and place the flat cap back over the filling.
For the frosting, place 3/4 cup softened butter and a pinch of salt in a large bowl. Beat on high speed for about 5 minutes until very pale and fluffy.
Add the powdered sugar and mix on low speed until combined, then increase to medium high speed and beat until light and fluffy.
Add the freeze dried raspberry powder, 2 tablespoons raspberry preserves, and 1 teaspoon vanilla to the frosting. Mix on low until incorporated, then on medium high until smooth and fluffy.
Transfer the frosting to a piping bag fitted with a decorative tip and pipe a generous swirl of raspberry frosting on top of each filled cupcake.
Garnish each cupcake with a fresh raspberry on top and serve.