Chocolate Salted Caramel Whoopie Pies

I love Whoopie Pies. Like, a lot. They’re a mess but the kind of mess that’s totally worth it.

I usually make the traditional Whoopie Pies, and they’re awesome. But I wanted to try something different this time. Salted caramel goes great with chocolate, right? So why not make a salted caramel filling??

Exactly. There is no argument to that question. So, here ya go:

Difficulty: medium
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Ingredients

PIES

1 2/3 cup flour
2/3 cup unsweetened cocoa powder – I usually used sweetened, but I feel like the lighter chocolate pairs better with the caramel of the filling
1 ½ t baking soda
½ t salt
4 T butter, softened to room temperature
4 T shortening
1 cup dark brown sugar, packed tightly (you can let it overflow a little – a little more is better)
1 large egg
2 t vanilla
1 ¼ cup milk
2/3 cup Sea Salt Caramel Chips *

FILLING

½ cup butter
1 cup dark brown sugar
6 T heavy whipping cream, divided
2 t vanilla
2 ½ cups powdered sugar, divided
½ t coarse sea salt

* Optional. But seriously – if you have them, why the heck not?

Directions

PIES

Combine the flour, cocoa powder, baking soda and salt. Put it to the side.

In a separate bowl, mix the butter, shortening and brown sugar. Not too long – just until they’re one uniform color. Then, increase the speed to medium and beat for three more minutes.

Add the egg and vanilla, beat on medium for another 2 minutes.

Add half the dry mixture from the other bowl and half the milk, beat on low until combined. Then beat in the remaining dry mixture and milk. Finally, if you’re adding them, stir in the chips with a wooden spoon so that they’re evenly distributed.

Drop a tablespoon of batter onto a baking sheet lined with parchment paper. Two things I’ve said about Whoopie Pie cookies before: 1 – these will spread a little so make sure they’re a couple inches apart from one another – figure 6 per sheet and 2 – try to use the same amount of batter each time – remember, these are going to be whoopee pies and you want both sides of the pie to be the same size.

Bake for about 10 minutes at 375. They’re done when the pies spring back if you press them lightly. Take out of the oven and let them cool on the sheet for 5 minutes before moving them to a wire rack to finish cooling.

FILLING

Put the butter in a medium saucepan and melt it over a low heat. Add in the brown sugar and half (3 T) of the heavy cream, turn the heat up to medium and whisk. Keep whisking until the sugar is completely dissolved. Once you get there, let the mixture boil for 3 minutes. You don’t have to whisk continually here, but make sure to do it every once in a while, just to make sure it doesn’t stick to the pan or burn. We’re pretty much making a caramel base here.

After 3 minutes, take it off the heat and pour it into a heat-proof bowl. Let it cool for a half hour or so – clean the pot, clean up your work space, or eat one of the whoopie pie cookies that must have broken while you were cooking them. Note – you want to get to the next step while the caramel is still warm. Just not boiling. You don’t want it to harden, otherwise it’ll be hard to mix. I let mine cool a little too long so there are bits of caramel in my filling. Not a deal-breaker, but not ideal.

Anyway, when the caramel is cooler, add in the remaining 3 T of heavy cream, the vanilla and 2 cups of the powdered sugar. Mix with a mixer until well blended. That MAY be all the sugar you need, or you may need to add a bit more in order to get a consistency that’s thick enough to pipe onto the cookies. Just keep adding the powdered sugar a little bit at a time until you get it to where you want it.

Once that’s done, pair up the cookie halves and pipe the caramel filling onto half of them. Take a pinch of the coarse sea salt (not too much), sprinkle that on top of the filling and then place the other cookie half on top and there you have it!