Caramel Filled Chocolate Cookies

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Who wouldn’t want to bite into a super chocolatey cookie, only to find a caramely surprise in the middle? Even though these cookies were a lot more time consuming and messy than usual drop cookies, it was totally worth the reactions I got once everyone bit into the centre. I had these bookmarked ever since I saw them over at Rebecca’s blog, indecisive baker.

I opted for caramilk instead of rolos because I think they just taste better.
Cadbury >> Hershey’s in my opinion.
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The only thing I was worried about was the caramel hardening after the cookies cooled because that would kind of defeat the purpose of putting a chocolate covered caramel in the centre in the first place. To retain the gooeyness of the caramel, I broke chocolate into squares and then froze them before wrapping in dough. By the way, I’m not sure if I just totally made that up, but I figured that if the caramel stayed cooler longer, it would cook less and therefore, not harden as much later. The frozen chocolate also helped with shaping the cookie because the dough stayed cooler longer and was less sticky. I would definitely recommend chilling the dough first before shaping.

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If only it wasn’t that obvious that there was something in the middle…
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Since I love Ina’s chocolate white chocolate chunk cookie recipe, I used hers minus the white chocolate instead. You can also use Rebecca’s recipe

Chocolate White Chocolate Chunk Cookies
Ina Garten
Makes 40 to 48 cookies

Ingredients
1/2 pound (1 cup/2 sticks) unsalted butter at room temperature
1 cup light brown sugar, packed (I used dark brown)
1 cup granulated sugar
2 teaspoons pure vanilla extract
2 extra-large eggs at room temperature (I used large eggs)
2/3 cup good unsweetened cocoa
2 cups flour
1 teaspoon baking soda
1 teaspoon kosher salt
1 1/2 pounds good white chocolate, coarsely chopped (I used white chocolate chips)
40-48 caramilk squares/rolos

Directions
Preheat the oven to 350 degrees F. (I baked at 335 F)
Cream the butter and both sugars until light and fluffy in the bowl of an electric mixer fitted with the paddle attachment. Dissolve espresso powder in vanilla extract. Add dissolved mixture, then the eggs, 1 at a time, and mix well. Sift together the flour, cocoa, baking soda, and salt and add to the butter mixture with the mixer on low speed until just combined.

Cover and place bowl into the refrigerator to chill for at least 2 hours. (you need to chill or else it’s too sticky)

Use a small cookie scoop (I use the Oxo brand, 2 tsp capacity) and unscoop it onto your hand. Flatten into a circle and place chocolate in the middle. Add another 1/2 a scoop to cover the top and seal the cracks.

Bake for 12 minutes (the cookies will seem underdone). Remove from the oven and let cool slightly on the pan, then transfer to a wire rack to cool completely.

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