Custom Order Kickoff: German Chocolate Surprise Cupcakes


Rich. Decadent. Sinfully delicious. It’s pretty fitting that I baked these bad boys on the heels of a trip to Vegas, because if Sin City had a cupcake – let me tell you – this would be it. There may not have been anything particularly “what happens in Vegas”-worthy about my time there (I was there speaking at a national election law conference), but these cupcakes were so devilish that they more than made up for it.

A few weeks ago, my friend and coworker, Erin (#teamlegal), wandered over to my desk and told me that she was throwing a going away party for two recently engaged friends from church. She had the food handled, but needed something sweet to add to the mix. Since I happen to specialize in sweet, she asked if I would be willing to bake the cupcakes for the party. I was so excited and honored that she thought of me (and would trust me with something like this!) and of course said yes. And with that, I officially had my very first custom order! Politics to Pastries was open for business.


Before I left for my trip, Erin and I got to work deciding just what kind of creation she wanted to concoct (ah, the beauty of custom ordering). The couple gave only one specification: chocolate. Lots of it. They did mention, though, that one of the bride-to-be’s favorites was German chocolate. I had been wanting to test out some German Chocolate Cupcakes but had always hesitated, primarily because (and Erin agreed) they’re not the prettiest cupcake variety. They’re usually served with the German chocolate filling spooned onto the top of the cupcake in what, quite frankly, looks like a big blob of goop (unbelievably delicious goop, but goop nonetheless). But these were for a party – and were my first project out of the gate – so they needed to be pretty. Very pretty. Then it hit me: fill the cupcakes with German chocolate filling, and do something custom for the couple on the top. It would hide the filling (also giving the guests an element of surprise, kind of like the curd) and make the cupcakes more decadent and personal in the process. I ran the idea by Erin. We had a winner.

To bring my perfect German Chocolate Cupcake vision to life, I decided to start with a moist but bouncy dark chocolate cupcake that would work nicely with a rich, gooey traditional German chocolate filling. To amp up the “rich” factor, I went with a chocolate cream cheese buttercream frosting. Erin had wanted a personal touch, so I decided to try my hand at some custom “H” toppers (for the couple’s last name) made out of melted white chocolate piped onto parchment paper and cooled until dry and hardened. I had also been obsessing over this unique 1 1/2 swirl piping technique I’d seen on Pinterest and Instagram that would perfectly complete the picture in my head. While I was a little nervous about trying a new decorating technique on an actual order (you know, something with slightly higher stakes than a Sunday night at 328 and G’s typical male “I mean it’s a cupcake, it’s good” critique), I had to go for it. Baking YOLO.


The dark chocolate cupcakes themselves came out BEAUTIFULLY! I couldn’t have been happier with these things. I got the recipe from the same blogger responsible for the unreal White Chocolate Whipped Cream frosting from last week’s Gender Reveal Cupcakes. I figured if her white chocolate frosting could be so heavenly, maybe the dark chocolate cupcakes she paired it with would be particularly, shall we say, sinful? I was right. The cake’s density and moisture were perfect for holding this thick, heavy filling, while the bounce and fluff it surprisingly maintained offered a wonderful balance of texture. Plus, they were so pretty that they basically begged you to eat them, even without frosting.

But of course, these were German Chocolate Cupcakes, so frosting and filling were beyond necessary. I went with a traditional German chocolate topping (or, in this case, filling!) with coconut and pecans. Once again, this filling recipe called for a little quality time with the stove, and you all know by now how I feel about that. I must actually be learning, though, because 1) I didn’t freak out during the process; and 2) this stuff came out exactly as it should have. There were no scorching mishaps and the mixture gradually thickened within the time frame it was supposed to, even with doubling the recipe. The second I removed the saucepan from the stove and mixed in the coconut and pecans, I knew this stuff would be downright dangerous. The excitement began to mount.


While the filling was cooling, I prepared the frosting. Since I knew I wanted a more structured frosting that could hold its shape and a garnish, I went with a chocolate cream cheese buttercream and substituted shortening for some of the butter. I learned from my Brown Sugar Cinnamon Poptart Cupcakes that substituting shortening for butter enhances the flavor of the frosting (since there is less of the butter’s flavor to get in the way), and provides volume and a much fluffier texture. Shortening is also better at withstanding heat – perfect for DC summers. Shortening was definitely the right choice here, and gave the frosting a perfect texture for what I had in mind. It also made the frosting that much more decadent, and allowed me to get these goodies over to the party without any major melting mishaps in the car. Look at me, I’m growing (again)!

Once the filling was cool, it was go-time. Now I had to bring the vision to life. I cored bigger-than-usual holes into the cupcakes to sufficiently accommodate the signature filling, and packed a hearty portion into each one. Then I replaced the cupcake tops, took a deep breath, and moved on to attempt the pipping swirl I’d been swooning over for a week. I think I literally held my breath to keep myself steady while I frosted each cupcake, but most of them came out great! I definitely got better as I went along and got into a rhythm with the timing and pressure applied to the piping bag, but they all ended up looking relatively uniform. I grabbed the little chocolate “H”s I had made the night before, and secured them slightly off-center where each frosting swirl ended, to provide a sort of asymmetrical-but-still-symmetrical effect all at once. Once I successfully placed the first few and saw that my vision was actually come to life, I got a little excited (i.e., overly excited, and I’m sure my new roommate – who had not yet experienced one of my baking endeavors – thought I was slightly crazy). I was so thrilled (and relieved!) with how they came out – I couldn’t wait to deliver them and show Erin!



As good as these German Chocolate Surprise Cupcakes looked, I promise you they tasted even better. They’re definitely rich, but not too rich. And all the flavors – well there are no words. You’ll just have to make them and see for yourself. Flat-out ridiculous. They may not have been in Vegas last week, but I would venture to say that the party guests felt like they hit the jackpot with these cupcakes. First custom order: check!

German Chocolate Surprise Cupcakes


Dark Chocolate Cupcakes (from Natasha’s Kitchen):

1 cup all-purpose flour
1 cup granulated sugar
2/3 cup unsweetened cocoa powder
1 teaspoons baking soda
1 teaspoons baking powder
1/2 teaspoon salt
1 egg, at room temperature
1/2 cup buttermilk
2 tablespoons plain Greek yogurt
1/3 cup extra light olive oil or canola oil (I used canola oil)
1/2 tablespoon vanilla extract
1/2 cup strong brewed coffee, hot

German Chocolate Filling (from Your Cup of Cake):

1 cup evaporated milk
1 cup sugar
3 egg yolks, lightly beaten
1/2 cup butter
1 ½ teaspoons vanilla extract
1 ½ cups chopped pecans
1 ½ cups flaked coconut

Chocolate Cream Cheese Buttercream (adapted from Your Cup of Cake):

4 ounces cream cheese
1/4 cup butter
1/4 cup shortening
2/3 cup unsweetened cocoa
3 cups powdered sugar
2 teaspoons vanilla extract
1 tablespoon milk or cream (if needed)


1. To make the cupcakes, preheat oven to 350˚F and line muffin pans with 16 liners. In a medium bowl, whisk together the flour, sugar, cocoa powder, baking soda, baking powder and salt, and set aside. In a large mixing bowl or the bowl of your stand mixer, beat together the egg, buttermilk, Greek yogurt, canola oil and vanilla for 1 minute on medium speed, or until well blended. With the mixer on low, slowly add the dry ingredients to the wet ingredients until no clumps of flour remain. The batter at this point will be rich and thick. Whisk in coffee and continue mixing until combined. Just to warn you, the batter will appear a little runny after adding the coffee. You didn’t screw up, that’s how it’s supposed to be!

Fill each cupcake liner 1/2 to 3/4 full, and bake for 18-20 mins or until tops are set and a toothpick comes out clean. Remove from oven and let cool 5 minutes before removing from cupcake pan to cool completely.

2. Now for the German Chocolate Filling! On medium heat in a sauce pan, combine evaporated milk, sugar, egg yolks and butter in a saucepan over medium heat, stirring constantly until thickened (about 15 minutes). It may start to simmer/boil several minutes in (mine even puffed up and got foamy for a minute before settling back down), but just push through and keep stirring. As long as you’re not blasting it on high heat, you should be fine. Once it’s sufficiently thickened to your satisfaction and thoroughly coats the back of a spoon, remove from heat. Stir in vanilla extract, pecans and coconut, and let cool. Take a deep breath in through your nose, because this stuff will smell amazing.

3. While the filling is cooling, prepare the frosting. Beat the cream cheese, butter and shortening in a large bowl for 4 minutes. Add cocoa, powdered sugar and vanilla extract and beat for 3 minutes. If it’s too thick, add some milk; if it’s too thin, add powdered sugar. You can also add more cocoa if it’s not dark enough for your liking.

4. Gather all of your ingredients, and core a generous hole in each of the cupcakes, reserving the cupcake tops. Fill each cupcake with a hearty scoop of German Chocolate Filling, replacing the cupcake tops when finished. Fill a pastry big fitted with the tip of your choice with the frosting, and pipe onto cupcakes as desired.

5. Grab a glass of milk and dig in!



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