Brown Sugar Cinnamon Poptart Cupcakes and a Glaze Debacle Well Worth It

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I’m not going to wind you all up here; I’m just going to come right out and say it: this really has to be the most unexpectedly amazing cupcake I have ever had. The flavor combination definitely sounds like it would be good, but, I mean, it’s brown sugar and cinnamon – how jaw-dropping could that really be, right? Yeah, that’s what I thought too…until I bit into it.

Suffice it to say that our house, which we have affectionately dubbed “328” after our street number, has a slight obsession with Brown Sugar Cinnamon Poptarts. Each of 328’s residents had each had their own storied history with these portable pastries (I personally had one for breakfast every day my senior year of high school. How my metabolism handled that – and all the SteaknShake I ate, for that matter – I will never know), but a new chapter began when a special delivery from our friend Kevin arrived in the mail. My roommate Christyn had been super helpful to him on a recent work trip  – a trip during which she also evidently professed her love for Brown Sugar Cinnamon Poptarts – and, as a thank you, he sent an entire case of the things straight to our house. We’re talking like 6 of the double boxes. It was like Christmas on a Tuesday.

Ever since that happened, Brown Sugar Cinnamon Poptarts have been a thing in our house, so when I was perusing Pinterest and came across a recipe for Cherry Poptart cupcakes, I immediately knew I needed to create a version in our favorite flavor. There weren’t really any recipes out there for Brown Sugar Cinnamon Poptart cupcakes in particular, so I just decided to piece one together on my own.

When I create a cupcake version of an already-established food, I usually try to deconstruct the flavors and then rebuild them in cupcake form, with each part of the cupcake bringing in one of the elements of the original. That way, when you bite into it, each separate element combines to give you the full experience of the original, but in cupcake form. My approach for these cupcakes was no different, so I set about trying to find the perfect way to combine and balance the brown sugar and cinnamon flavors, the gooey center, and that famous Poptart icing that makes them oh-so-sweet. I ultimately decided to do a simple brown sugar cupcake and fill it with a thick, gooey, cinnamon-brown sugar filling. To replicate the hard icing shell, I would top the cupcake with a brown sugar glaze, and then pile on some cinnamon buttercream, with a little Poptart bite for garnish (obviously).

Now I should warn you that these were slightly labor intensive. That was partially made more true because I completely botched my first attempt at the brown sugar glaze and had to start over (oopsies), but with all the different elements, these will take some time regardless. That being said, it is SO worth it!

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The brown sugar cupcakes were pretty self explanatory, as was the icing. The filling and the glaze, however, were more of a challenge this time around. The glaze especially – we’re talking curd-level anxiety here, people. The tricky part about the filling was that the original recipe I pulled it from used it inside of homemade poptarts, in which it underwent baking inside of the pastry. I wanted to use this filling without any baking time, so I knew it would be an experiment to see whether that changed anything. I made the filling as directed, and it seemed to be a suitable consistency – not too much of a syrup, but definitely not a paste. In an effort to maybe meld the flavors together a bit, I cooked it in the microwave for a minute or so on 30% power, in hopes that that would do the trick. To be frank, I have no clue whether it made any difference or not, but it made me feel better. I let it sit while I cored the cucpakes, and it thickened up to a perfect gooey consistency. Then I moved on to the glaze.

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The directions seemed simple enough: melt butter, add brown sugar, bring to a boil, decrease heat, add milk, bring back to a boil, cool to lukewarm then add powdered sugar. Well, let me tell you, that butter and brown sugar mixture will go from warm to popping in a fraction of a hot second, and start to burn quickly if you’re not careful with your stove’s heat level. Glaze: 1; Christine: 0. Note to self: don’t add cold milk to violently boiling brown sugar and butter mixture (don’t judge, it had been a long day of baking and blog post-drafting). Lesson learned. Just be very careful with your heat level and err on the side of caution, and this really is totally doable. My second attempt went much more smoothly. The other quandary that arose with the glaze was that it didn’t reach any sort of smooth consistency when I added the powdered sugar. It was solid and clumpy and not glaze-like at all, which at this point was just salt in my “baking fail” wound. Just as a last-ditch effort before I surrendered to the glaze gods, I added a little water and beat it with the mixer one last time. Boom. We had a liquid! I added just a touch more and that did the trick. The only remaining issue was that it turned out to have much more of a brown butter flavor than I had anticipated, so I was nervous it would disrupt the balance I was going for with these cupcakes. While it definitely didn’t “disrupt” anything (I have absolutely nothing bad to say about these cupcakes), next time I probably will try to tweak the glaze to bring out more brown sugar, less brown butter.

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Once all the different elements were prepared, the assembly itself was a piece of cake (see what I did there?). After I topped each high-hat icing swirl with a poptart bite, it was only a matter of taste testing (for quality control purposes, of course). Now after all the drama that went down during this baking process, I wasn’t overly-eager to try one at first (I understandably just needed a little space), so I made my friend Erick come over to pick some up and do the honors. Once he started in with his animated critique, though, my curiosity got the best of me. I made myself cut a little piece of one of the cupcakes to try, not expecting anything mind-blowing. Yeah, that whole “I really don’t even want this right now” turned into “I just inhaled that entire cupcake” real quick. These flavors balance out perfectly and really do all combine to give you the whole Brown Sugar Cinnamon Poptart experience in every bite. The brown sugar cupcake was the perfect consistency for this uh-mazing, gooey, cinnamon-sugary filling, which played off the brown sugar glaze and fluffy cinnamon icing incredibly. When I had a little bite of the poptart garnish at the end of the cupcake, the resemblance was uncanny. I don’t say this often, but these kinda nailed it.

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These will definitely add a new page to 328’s Brown Sugar Cinnamon Poptarts chapter. Now I need to figure out how to ship a batch to Kevin, this time as a thank you to him for the inspiration (I’m lookin’ at you, Benacci).

Brown Sugar Cinnamon Poptart Cupcakes

INGREDIENTS

Brown Sugar Cake (From Sally’s Bake Blog):

1 and 2/3 cup all-purpose flour (be careful not to over-measure!)
1/2 teaspoon baking powder
1/4 teaspoon baking soda
1/2 teaspoon salt
1 cup light brown sugar
1/2 cup (1 stick) unsalted butter, melted
1 large egg, at room temperature
1/4 cup yogurt (I used plain, but you can use greek, or sour cream)
3/4 cup milk
1 Tablespoon vanilla extract

Cinnamon-Brown Sugar Filling (from BraveTart):
3 ounces fresh bread crumbs
1/16 of a Tablespoon unsalted butter, melted
1/2 cup brown sugar
4 teaspoons cinnamon
2 1/2 ounces corn syrup
1 Tablespoon vanilla extract
1/2 teaspoon kosher salt

Brown Sugar Glaze (from Sweet Treats & More):
1/4 c butter
1/2 c brown sugar
1/8 c milk
1/2 c sifted powdered sugar

Cinnamon Sugar Frosting (from Life Love Sugar):
1/2 cup butter
1/2 cup shortening
4 cups powdered sugar
2 1/2 tsp cinnamon
3/4 tsp vanilla extract
1-2 tbsp water or milk

INSTRUCTIONS

1. First, bake the cupcakes. Pre-heat oven to 350 and line a cupcake pan with liners. In a medium bowl, whisk the flour, baking powder, baking soda, and salt, and set aside. In a large microwave-safe bowl, melt butter in the microwave. Whisk in the brown sugar vigorously until no lumps remain. Whisk in egg, yogurt, milk, and vanilla extract until combined. Slowly mix in dry ingredients until no lumps remain. This batter will be thick. Fill each cup 3/4 of the way full, and bake for 20 minutes, or until a toothpick inserted in the center comes out clean. Allow to cool completely before filling.

2. Next, prepare the gooey filling. Pop a several chunks of bread (a little stale is actually better!) in a food processor and grind/pulse until you have fine crumbs. Mix all ingredients together in a small bowl until fully combined. Yes, that’s it.

3. Now comes the fun part – the glaze. Melt butter over low heat in a small sauce pan. Stir in brown sugar and bring to a boil.  Immediately lower heat to low-medium and continue to boil for two minutes, stirring constantly. Be careful that the mixture doesn’t start to burn. If boiling is too intense, lower the heat! After 2 minutes, carefully add the milk and return to boil, still continually stirring. Remove immediately from heat, and set aside to cool to a lukewarm temperature. Remember that all of this happens very quickly! The entire process lasts no longer than 4-5 minutes.

Once the mixture has cooled down, gradually stir in the powdered sugar and beat with a mixer until smooth.  Add more powdered sugar if needed, or, it seems too thick (like mine definitely was!) add a little bit of warm water until you reach the desired consistency.

4. To make the frosting, beat the shortening and butter until smooth. Slowly add 3 cups of powdered sugar, one cup at a time, mixing until combined between each addition. Mix in the cinnamon, vanilla extract and 1 tablespoon of water. Add the rest of the powdered sugar and mix until smooth, light and fluffy. Add more water if necessary to achieve your desired consistency.

5. Assemble the cupcakes! First use a paring knife to core the cupcakes, preserving the tops. Add the filling, replacing the touch of each cupcake once you’re done. Next, spoon a dollop of the brown sugar glaze onto each filled cupcake, and spread evenly. Allow the glaze to harden a bit, and then pipe the frosting on as desired (I used a Wilton 1M tip here). Finally, break off pieces of a Brown Sugar Cinnamon poptart and place on top for garnish.

6. Serve and enjoy!

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