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Chocolate Caramel Pocket Cookies

Chocolate Caramel Pocket Cookies on a blue plate

For my recent birthday, I received five (yes, five) new cookbooks. One of these five, from Quinn, was The Ultimate Chocolate Cookie Book. Of course, I’m sure this was a completely unselfish gift. Surely he’s not trying to encourage me to make more cookies. Anyway, I thought my first recipe to try should be something Quinn would really like. He’s a big caramel fan, so I knew he would like these.

These cookies have a caramel center. To make the center, store-bought chewy caramels do the trick. You’ll need about 36 of these, with each one cut in half. I recruited Quinn for caramel duty. Baking was delayed as he stacked them for their photo shoot. Baking was further delayed when I foolishly remarked that he could make a little “Caramelhenge” out of them. Ah, such is life with Quinn.

These were, as predicted, a big hit with Quinn. Not the prettiest cookies I’ve ever seen. A bit lumpy. Some looked like standard cookies, while some looked like cookies wrapped around caramels. I’m not really a big caramel fan, so I think I would have preferred a different filling. The recipe suggested some variations – chocolate-covered almonds, Hershey’s kisses, hazelnuts… you get the idea. In hindsight, I would have made part of these with different fillings. It would be kinda like the Whitman’s Sampler of chocolate cookies. Hmmm… perhaps I’ll give it a try some day.

Chocolate Caramel Pocket Cookies

Yield 36 cookies
Prep Time 20 minutes
Cook Time 12 minutes
Total Time 32 minutes

These soft and chewy chocolate cookies are stuffed with a rich caramel filling. This recipe is great for quick and easy treats!

Chocolate Caramel Pocket Cookies on a blue plate


  • 36 soft caramels
  • 2 & 1/4 cups (270g) all-purpose flour
  • 1/2 cup (42g) unsweetened cocoa powder, sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 cup (226g) unsalted butter, softened
  • 1/2 cup (100g) granulated sugar
  • 1/2 cup (100g) firmly packed dark brown sugar
  • 1 large egg
  • 1 large egg yolk
  • 2 teaspoons vanilla extract


  1. Preheat oven to 350°F. Line baking sheets with parchment paper or silicone liners.
  2. Cut each caramel in half and set side.
  3. Whisk together the flour, cocoa, baking powder, and salt. Set aside.
  4. Using an electric mixer on medium speed, beat the butter until light and fluffy. Add the sugars and mix well. Mix in the egg and egg yolk; then, add vanilla.
  5. Reduce the mixer speed to low. Add the flour mixture and mix just until combined.
  6. Form a tablespoon of dough into a circle. Place 2 caramel halves in the center of the circle. Fold the dough around the caramels, making sure to seal well. Place each cookie on the prepared pans, leaving about 2 inches between cookies.
  7. Bake one pan at a time for 10 to 12 minutes or until the cookies are set.
  8. Cool the cookies on the pans on wire racks for 5 minutes. Then transfer the cookies from the pans directly onto a wire rack to cool completely.


Recipe adapted from The Ultimate Chocolate Cookie Book.

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    20 Comments on “Chocolate Caramel Pocket Cookies”

  1. I love caramel so much!! I can’t bake these because I would probably eat them all in one sitting!

  2. Oh and HAPPY BIRTHDAY!!!!!!!

  3. Hi Jennifer,
    your blog looks great!
    Wow, FIVE cookbooks…I’m really jealous now =)
    Are they all so nice?
    These cookies look by the way pretty good to me, can’t wait for your variations! =)

  4. Wow, these sound terrific! Caramel and chocolate are such a yummy pairing!

  5. Nicole, thanks for the birthday wishes!

    Julia, I think the cookbooks will all be great. I already have quite a “to try” list. I’m trying to think of some good variations on these cookies.

    Gilly, they are good and, best of all, easy!

  6. Happy belated birthday! You should consider submitting these amazing cookies for SHF #23. It’s being hosted by Alanna of A Veggie Venture.

  7. whoa. a caramel center?

  8. These had to be gooey and delicious! You have a lovely website, Jennifer. (thank you for your kind words about my baby site) 🙂

  9. i love the idea of a fun center. maybe a reese’s cup?

  10. Ivonne – Thanks for the birthday wishes. I’ll be sure to get these sent in to SHF.

    Jen – Thanks for stopping by!

    Connie – Oh, yeah. A lovely, gooey caramel center.

    Rachel – Quinn and I were actually saying today that we think these would be a great use of leftover Halloween candy. Hopefully, we won’t forget and we’ll see these again post-Halloween.

  11. I would have loved to have made these the week I was obsessed with caramel.
    Looks great.

  12. Ooo, thanks for the recipe. I am so going to make these!

  13. Hi Jennifer, I found your site via a comment you posted on sweetnicks. I wish I had seen it earlier, it’s just so delightful! You’ve done such a wonderful job with it, I’m really excited about exploring it some more. And these cookies look excellent! 🙂

  14. Oh my god, what a brilliant idea for a cookie – I’d never thought of surrounding cookie dough with a treat!

  15. That oozing caramel looks so delicious! I love caramel, especially with chocolate so this is my kind of cookie. I bet some kind of peanutbutter filling would be good too. Make it like a Reese’s, in cookie form.

  16. holy cow…those look incredible…

  17. These look incredible, but like Nicole said, I’d worry I’d eat ’em all in one sitting. 🙂 It’s got me thinking about other candy stuffed inside cookies… maybe Junior Mints?!

  18. Great idea for a lovely surprise!

  19. Great SHF entry! The line about the Whitman Sampler was great–I had been thinking along those lines when I read Karen’s (from A Couple of Tarts) entry: Rolo Cookies. Candy and cookies together. Just as it should be! *smile*

  20. I love the Caramelhenge. It actually makes a really pretty picture with the way the light is hitting it!

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