Chocolate Caramel Pocket Cookies

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

Prep Time: 20 minutes

Cook Time: 12 minutes

Yield: 36 cookies

Chocolate Caramel Pocket Cookies


  • 36 soft caramels
  • 2 & 1/4 cups all-purpose flour
  • 1/2 cup cocoa powder, sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 cup unsalted butter, softened
  • 1/2 cup granulated sugar
  • 1/2 cup dark brown sugar
  • 1 large egg
  • 1 large egg yolk
  • 2 teaspoons vanilla extract


Preheat oven to 350°.

Cut each caramel in half and set side.

Mix together flour, cocoa, baking powder, and salt.

In a separate bowl, beat butter until softened. Add sugars and mix well. Add egg and egg yolk; then, add vanilla.

Once this is mixed, add the flour mixture and mix well.

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 an ungreased baking sheet.

Bake for 10 to 12 minutes. Cool on wire racks.


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  1. Nicole August 30, 2006 Reply

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

  2. Nicole August 30, 2006 Reply

    Oh and HAPPY BIRTHDAY!!!!!!!

  3. julia August 30, 2006 Reply

    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. gilly August 30, 2006 Reply

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

  5. jennifer August 30, 2006 Reply

    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. Ivonne August 30, 2006 Reply

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

  7. connie August 30, 2006 Reply

    whoa. a caramel center?

  8. Jen August 30, 2006 Reply

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

  9. rachel August 30, 2006 Reply

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

  10. jennifer August 30, 2006 Reply

    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. peabody August 31, 2006 Reply

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

  12. Hilary August 31, 2006 Reply

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

  13. Christine August 31, 2006 Reply

    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. Ellie September 1, 2006 Reply

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

  15. Natalia September 1, 2006 Reply

    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. Elizabeth September 18, 2006 Reply

    holy cow…those look incredible…

  17. JBD September 24, 2006 Reply

    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. Cin September 25, 2006 Reply

    Great idea for a lovely surprise!

  19. Josie September 26, 2006 Reply

    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. KT September 26, 2006 Reply

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

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