Good Eats and Sweet Treats from My Small Boston Kitchen

Salted Caramel-Stuffed Chocolate Chip Cookies

It seems to me that cookies are synonymous with the holiday season. They’re a great office gift, a perfect post-holiday-meal treat, and a much-needed pick-me-up during these hectic days of December. For this reason and many others, The Great Food Blogger Cookie Swap is kind of a genius idea. I love the idea of it — bake three dozen cookies, send one dozen each to three other bloggers, and receive three dozen cookies yourself. Sounds pretty amazing, right? But I know myself, and this time of year things get so busy that I wasn’t sure I should commit. Intrigue, and the idea of loads of delicious cookies, got the better of me this year though, and I decided to partake in the 5th annual cookie swap.

As expected, I completely procrastinated with this project. To be fair, I often do my best work (whether it’s professional or on this blog) when I’m under pressure or working on deadline, so these cookies turned out darn good, but I was definitely down to the wire with this one. I waited until four days before these cookies needed to be shipped before even picking out a recipe to make, and after one rather large mishap during the baking process, I left myself with only one day to spare.

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

The cookies came out beautifully, and made it into the mail just in the nick of time. Behind the scenes, however, was a different story entirely.

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

If you’re ever tried to stuff something heavy like caramel into your cookies, then you can probably appreciate my struggle. Late one Sunday evening, after I’d picked out my recipe and gotten all the ingredients, I put the cookie dough together and was feeling good. According to the recipe I was using, I should have more than enough cookies, so I really thought it was smooth sailing.

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

After the dough finished chilling, I started to assemble the cookies, and when all was said and done, realized I only one one extra. 37 cookies when I needed 36. No big deal, I thought. I’ve baked cookies a thousand times. I’ve got this in the bag! So into the oven they went, and about 12 minutes later, out come these perfect little beauties. After a sprinkle of flaky sea salt and several minutes cooling on the baking sheets, I transferred them to a wire cooling rack and started the next batch.

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

Somewhere in the middle of this process, I changed what kind of cooling rack I was using. This new one had wider spaces between each wire support, but I didn’t think anything of it… until each of the cookies I placed on that cooling rack started to implode. At first it was just one cookie, and I had one to spare. I tried to stay calm as I scrambled to piece it back together. But then another started to go — the caramel center oozing quickly through the wide wire rows, and plopping indelicately onto the countertop below. I started wailing. Literally. The chain of hysterics and curse words that came out of my mouth prompted one of my roommates to come running into the kitchen, but the cookies were beyond saving. I’ll spare you the rest of the details, but needless to say, long after bedtime had come and gone, I remained in the kitchen starting a new batch of dough.

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

Green plate: first batch cookie. Red plate: second batch cookie (my favorite).

I’d run out of caramels for the centers, and run out of regular chocolate chips, so I used larger dark chocolate chips in this new batch, and let it sit in the fridge overnight so I could run out during work the following day for new caramels. It turned out to be a blessing in disguise, because the second batch of dough ended up being my favorite. The dough really benefited from an overnight fridge stay, and the new caramel — Kraft brand instead of the store-brand kind from Target (which baked up way too hard in the cookies) — was much softer and more pliable after baking. The second batch of cookies even had a prettier appearance (see above), and after those were all baked up, and the cookies were nestled carefully into their shipping containers, I felt pretty proud of the effort as a whole.

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

These cookies though? They’re really super duper amazing. Each time I ate one, I heated it up a bit, so the chocolate chips got soft and the caramel was tender and gooey. The salt on top really did me in, and I could not get enough. Everyone who tried these cookies swooned over them, and I loved them so much I’m bringing them in for my coworkers next week as a holiday treat.

Salted Caramel-filled Chocolate Chip Cookies - Sweetly Serendipity

Hopefully next year’s Great Food Blogger Cookie Swap process will be a bit smoother from start to finish, but I can’t imagine finding a cookie recipe to beat this one.

Interested in how you can participate next year? Sign up to receive updates when registration begins!

Salted Caramel-stuffed Chocolate Chip Cookies

Ingredients

  • 12 tablespoons (1 1/2 sticks) unsalted butter, softened
  • 3/4 cup packed brown sugar
  • 1/4 cup granulated sugar
  • 1 teaspoon vanilla extract
  • 1 egg
  • 2 cups all-purpose flour
  • 1 3.4oz box instant vanilla pudding mix - dry, not prepared (must be the Instant kind)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 2 cups semi sweet chocolate chips
  • 24 soft caramels (I prefer Kraft square caramels), unwrapped
  • Flaky sea salt

Directions

  1. In a large bowl (or the bowl of a stand mixer fitted with the paddle attachment), add the butter and sugars and beat together for 1-2 minutes until nice and fluffy. Add the vanilla and the egg and continue mixing until well incorporated. Scrape down the sides of your bowl and beat again just to be sure all the ingredients are incorporated.
  2. In a separate medium bowl, add the flour, pudding mix, baking soda, and salt, and stir to combine. Add the dry ingredients to the wet ingredients, and mix until all of the ingredients are incorporated. Add the chocolate chips and fold in with a spatula or wooden spoon. Cover dough and place in the refrigerator for at least 1 hour (overnight is even better if you've got the time).
  3. When you're ready to bake the cookies, preheat your oven to 350 degrees F and line baking sheets with a silicon baking mat or parchment paper. Lightly greased sheets should work as well.
  4. Roll about 3-4 tablespoons of cookie dough into a ball, and continue until you've rolled all of the dough. Ideally you'll have about 48 balls of dough. For each cookie, take one ball of dough, and use your thumb to make an indent in the center, then place a caramel there. Cover it up by another ball of dough, and press the two pieces of dough together so that the caramel is sealed inside. Form the dough into a round disc as best you can. Repeat with remaining dough balls.
  5. Place each ball of dough 3-4 inches apart on your baking sheet, and bake for about 12-14 minutes, until the cookie is set but looks just cooked through. Remove from the oven and sprinkle with sea salt immediately. **Allow to cool for at least 10 minutes on the baking sheet** (this step is super important), and then transfer to a cooling rack and allow to cool to room temperature.
  6. These cookies will store well in an airtight container for a few days, and freeze nicely. To serve, I heat mine up just a bit so the caramel centers are nice and gooey.
http://www.sweetlyserendipity.com/dessert/cookies/salted-caramel-stuffed-chocolate-chip-cookies/

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