Recently I wanted to send a gift over to our babysitter to thank her for taking such wonderful care of Andrew this year.  It was tough to figure out what to give her that could really express just how grateful we are but I finally settled on a spa gift certificate for some well-deserved pampering.  I also felt that I should send something her whole family could enjoy, since they have all been so loving and welcoming to Andrew.  The answer for this was a no-brainer – cupcakes!  Her three girls love when I send over cupcakes and the whole family LOVES chocolate, so I settled on these chocolate raspberry cupcakes.  They are a basic devil’s food cake, filled with raspberry jam, topped with raspberry jam buttercream.  The special surprise on top is that the fresh raspberries themselves are filled with ganache, hence the “truffle” in the title – divine!  Chocolate and raspberry are so clearly made for each other, and these really turned out wonderfully.  

Of course, I wasn’t completely on my game when I made these and accidentally filled about half of them with strawberry jam (in my defense, the jar looks identical!)  They still tasted great though.  Next time I will make a few changes.  The first would be to pipe the filling into the cupcakes rather than use the cone method.  This cake is very moist and crumbled quite easily when cut into, making it less than ideal for the cone method.  I think piping it in with a pastry bag would be much more effective for a neater result.  Also, I strongly prefer using fresh/frozen raspberries rather than jam in recipes, so next time I think I’ll try the filling from this Smitten Kitchen recipe.   Enjoy!

Note: I have been gone on a week-long beach vacation since making these, and have consequently forgotten how many the batch yields.  I know that I made 16, but I cannot remember if there was extra batter left over (I think there was).  Sorry to not post a more accurate estimate! 

Chocolate Raspberry Truffle Cupcakes
For the cupcakes:
9 tbsp. unsweetened cocoa powder
1 1/2 cups cake flour
1/2 tsp. salt
1 tsp. baking soda
1/4 tsp. baking powder
8 tbsp. unsalted butter, at room temperature
1 1/2 cups granulated sugar
2 large eggs, at room temperature
1/2 cup strong coffee (or water)
1/2 cup whole or low-fat milk

For the filling:
Seedless raspberry jam

For the raspberry truffles:
2 pints fresh raspberries
5 oz. semisweet or bittersweet chocolate, finely chopped
1/4 cup seedless raspberry jam 
1/3 cup heavy cream 

For the frosting: 
16 tbsp. unsalted butter, at room temperature
6 cups powdered sugar
1/2 cup seedless raspberry jam
Pink icing color (optional) 

To make the cupcakes, preheat the oven to 350° F.  Line two cupcake pans with paper liners.  In a small bowl sift together the cocoa powder, cake flour, salt, baking soda, and baking powder.  In the bowl of a stand mixer fitted with the paddle attachment, cream the butter and sugar on medium-high speed until light and fluffy, about 5 minutes.  Mix in the eggs one at a time, scraping down the sides of the bowl between additions.  

In a liquid measuring cup, combine the coffee and milk.  Add half of the dry ingredients to the mixer and mix on low speed just until incorporated.  Stir in the coffee-milk mixture and mix until combined.  Add in the remaining dry ingredients, again mixing just until incorporated.  Divide the batter evenly between the cupcake liners, filling the cups about 3/4 full.  Bake for 20 minutes, or until a toothpick inserted in the center comes out clean.  Transfer to a wire rack to cool completely. 

Once the cupcakes have cooled completely, heat some raspberry jam just enough to allow for easy stirring and smooth texture (I do about 20-30 seconds).  Transfer the jam to a pastry bag fitted with a large plain tip, poke into each cupcake and pipe a small amount inside.

To make the raspberry truffles, rinse fresh raspberries and transfer to a baking sheet lined with paper towels.  Gently shake the berries around to remove excess water.  Place the chocolate and jam in a small heatproof bowl.  Bring the cream to a boil in a small saucepan.  Remove from the heat and pour over the chocolate and jam.  Let stand for about 3 minutes.  Whisk together gently until smooth.  If any unmelted lumps remain, microwave a few seconds and whisk again.  Let the ganache cool a bit until it has thickened slightly (enough to be piped through a pastry bag).  Once it has reached the right consistency, transfer the ganache to a pastry bag and pipe into the center of the clean raspberries.  Refrigerate at least 15 minutes to set.

To make the frosting, place the butter and jam in the bowl of a stand mixer fitted with the paddle attachment.  Cream on medium-high speed until well incorporated, about 2 minutes.  Sift in the powdered sugar and mix until smooth.  Tint with icing color as desired.

To finish the cupcakes, frost with the raspberry jam buttercream and top with a few of the raspberry truffles.   

Source: adapted from Hello! Baker, originally from David Lebovitz and Culinary Concoctions by Peabody