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Everyone’s favorite…Crinkly Caramel Stuffed Brownie Cookies…for your Tuesday night pre-holiday cookie baking. Homemade crinkly brownie cookies, made with sweet milk chocolate, a touch of coffee, stuffed with gooey chocolate-covered caramels, then baked to perfection. Each cookie is finished with flaky sea salt for a cookie that’s salty, sweet, and dangerously delicious. Each bite is crisp and crinkly on the top, but soft and gooey in the center. There’s nothing not to love about these sweet crinkly caramel stuffed brownie cookies.

overhead photo of Crinkly Caramel Stuffed Brownie Cookies | halfbakedharvest.com

Happy Tuesday everyone!! I thought we’d brighten up the day with some of my favorite cookies. These are truly that melt in your mouth cookie that we could all use today.

These cookies, plus a warm mug of hot chocolate, or maybe a pumpkin latte. Yes, sounds like the perfect way to de-stress. Whether it’s today, tomorrow, or throughout this busy end of the year holiday season, these should be your go-to. They’re sweet, perfectly hinted with coffee, and stuffed with delicious milk chocolate caramel chunks.

prep photo of Caramel Stuffed Brownie Cookie before baking

One of my favorite cookies – and my family’s too. Already excited to include these in my 2020 holiday cookie box in just a few short weeks! I know it’s only November 3rd, but I’m officially kicking the holiday baking season off with these cookies. They’re decadent in all the best ways. And yes, you do need to make them, preferably several times over the next few weeks! As I’ve already said, this year needs all the holiday cheer we can give it, so why not start a little early. Right?!

And with that, let’s get to the details!

prep photo of Caramel Stuffed Brownie Cookies before baking

Everything you need to know about baking these cookies.

First things first, start with the chocolate. You need a lot of it. I used a mix of milk chocolate, semi-sweet chocolate, and even some cocoa powder. I really wanted these cookies to resemble my favorite crinkle top brownies, so I used a very similar set of ingredients for the dough.

Simply melt together salted butter (my baking secret) with both of the chocolates. It’s going to seem like a lot of chocolate, but trust me it’s all going to turn out great.

Once the chocolate is melted, beat the eggs until they’re light and creamy. This step is KEY if you want a crinkly cookie, so don’t skip it. Once you see the eggs turn pale in color, add in that melted chocolate, then all of the dry ingredients.

overhead photo of Crinkly Caramel Stuffed Brownie Cookies

Mix and done, that’s your brownie-cookie dough.

So simple. But here’s the hard part, we need to chill the dough to help it stiffen up before rolling it out. To speed up the process, I just stash the dough in the freezer for thirty minutes until it’s firmed up.

Once the dough is chilled, roll it out, and stuff each dough ball with a sweet milk chocolate caramel, then bake!

side angled close up photo of Crinkly Caramel Stuffed Brownie Cookies

What I love about these cookies is that they’re easy to make, but yet they feel fancy. Everyone thinks they likely took hours to make, when they’re actually super simple.

But my favorite part? These are just perfectly crinkly on top, but also soft and gooey in the center, with caramel melting out. The best kind of cookie…decadent. But it’s what we need today. Perfect for Tuesday baking, our Thanksgiving table, holiday cookies boxes, and Christmas baking.

So, what do you think? Tuesday night baking?

Then take the leftovers to work and make everyone’s day. You should do this. It is the season of giving!

overhead close up photo of Crinkly Caramel Stuffed Brownie Cookies

Looking for other Thanksgiving cookie recipes? Here are my favorites: 

Chai Spiced Maple Sugar Cookies with Browned Butter Frosting

Slice n’ Bake Salted Chocolate Butter Pecan Cookies

Pecan Pie Cookies with Butter Pecan Frosting

Lastly, if you make this Crinkly Caramel Stuffed Brownie Cookies, be sure to leave a comment and/or give this recipe a rating! Above all, I love to hear from you guys and always do my best to respond to each and every comment. And of course, if you do make this recipe, don’t forget to tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!

Crinkly Caramel Stuffed Brownie Cookies

Author: Tieghan Gerard
Prep Time 20 minutes
Cook Time 10 minutes
Total Time 1 hour 30 minutes
Servings: 24 cookies
Calories Per Serving: 456 kcal

Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.

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Ingredients

US Customary - Metric

Instructions

  • 1. In a microwave-safe bowl or glass measuring cup, melt together the butter, milk chocolate, and chocolate chips until melted and smooth. Let cool completely. *This can also be done on the stove.
    2. In a large mixing bowl, beat together the eggs and sugar, beating on high until pale in color, about 3 minutes. Add in vanilla extract, instant coffee (if using), and the melted chocolate/butter, beating until combined. Add the flour, cocoa powder, baking soda, and salt, mix until just combined. The batter with be very loose. Divide the dough in half. Cover each ball of dough and chill 1-2 hours in the fridge or overnight, until firm. Preheat the oven to 350° F. Line a baking sheet with parchment paper. 
    3. Working with 1 dough ball at a time (leave the other in the fridge), roll the dough into tablespoon size balls. Flatten the dough slightly into a round and add the chocolate covered caramel. Scoop another tablespoon of dough out and flatten it slightly. Place the dough over the caramel, sealing the edges together. Place 3 inches apart on the prepared baking sheet. If the dough softens, stick it in the freezer for a few minutes to re-chill it.
    4. Bake for 10-14 minutes, until just set on the edges, but puffed in the center. Let the cookies cool on the baking sheet. They will continue to cook slightly as they sit on the baking sheet. Sprinkle with flaky salt (if desired). Eat warm (highly recommended) or let cool and store in an airtight container for up to 4 days. 

Notes

Caramels: I use Dove milk chocolate caramels. 
Freezing: the cookie dough balls can be frozen for up to 3 months. Thaw, then bake as directed. 
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Comments

  1. 4 stars
    Are you able to give a more accurate description of what the consistency of the “dough” should be like before cooling?

    I made these last night, and they were yummy! But I was shocked by how liquidy the batter was before the cooling step and ended up adding a bunch more flour to thicken it. I can see how it solidifies when cooled, but even then, would love to know how moist etc the dough should end up being in order to create the right texture in the cookies

    Reply

    1. Hi Sienna,
      Thanks for giving these cookies a try! Please refer to the photos above to see what the dough should look like. The dough will be loose, but once chilled it should be firm. I hope this helps! xTieghan

      Reply

  2. I’d like to make the dough and refrigerate it per instructions. Then take it out, roll the balls adding the chocolate caramel and then refrigerate the individual balls so that I can bake them while dinner is being served. That way they’ll be warm out of the oven for dessert. Any reason that wouldn’t work?

    Reply

      1. Great! Thanks. Next question…my “dough” is more of a batter. I’m wondering how I’m supposed to get it into a “ball” to refrigerate it? Maybe I went wrong somewhere on the recipe? What I did was pour it into two small bowls. Threw one in the freezer and one in the fridge. Guess I’ll find out if it works when I pull it out to roll it and form the balls.

        PS Congrats to your brother and Hannah. What great representatives of the USA!

        Reply

  3. 5 stars
    An amazing cookie! I put them in our Christmas cookie boxes for coworkers, and they were everyone’s favorite. I was worried when we first mixed them that it wouldn’t come together, but the chill time really firms up the dough.

    Has anyone tried a 1-to-1 GF option with success? My sister is GF and I wanted to make her these for her engagement party.

    Reply

    1. Hey Sydney,
      I love to hear that this recipe was a hit, thanks a lot for giving it a try!! Yes, GF flour will work well for you! xxT

      Reply

  4. 5 stars
    I made these yesterday using milk duds because I couldn’t find anything else and it came out great!! These cookies are fantastic!

    Reply

    1. Hey Emilie,
      Totally, that will work well for you! Please let me know if you give the recipe a try, I hope you love it! xTieghan

      Reply

  6. How do these hold up when baked and then frozen? Doing some baking for a wedding and think these would be a hit!

    Reply

    1. Hey Elise,
      I think that would work well for you! Let me know if you give the cookies a try, I hope you love them! xTieghan

      Reply

  9. 5 stars
    I make a Christmas cookie box for all my neighbors every year inspired by your recipes and a few of my other favorite bakers. I debuted this recipe for my 2021 box and it was a HIT! Easily everyone’s favorite. I doubled the recipe, but still only divided the dough in two. Chilled in the fridge overnight and it was fine to roll the next day. I coated my hands in a thin layer of cooking spray or vegetable shortening as well as the spoon I was using to scoop the dough and that also seemed to help the dough from becoming too sticky to form into balls. This recipe will definitely be in my cookie box for years to come!

    Reply

    1. Hey Summer,
      Awesome! Love to hear that you liked the recipe, thanks a bunch for trying it out! Thanks for sharing what worked well for you. Happy Holidays! xx

      Reply

  10. 5 stars
    Love love love this recipe! I tried it with peanut butter instead of caramels inside and it worked great. I mixed PB & a little icing sugar and piped it into the centre of each dough ball before sealing. YUM.

    Reply

  11. 5 stars
    These came out great – so delicious! The dough was a little tough to work with, but as long as you have enough time to put it in the fridge when you need it, it worked great (I made the dough & put it in the fridge overnight; it was TOO cold then, so I found that when I was making the dough balls I had to leave it out on the counter to warm up).
    Silly q – the recipe is for 24 cookies, but it says to have 36 caramels. Did I miss something or do you just use 24? it kind of looks like from some of the pictures that you may shave some chocolate on top of the formed dough balls?

    Reply

    1. Hey Whitney,
      Happy Sunday! So glad to hear that this recipe was enjoyed, thanks for making it! Since everyone makes their cookie sizes slightly different, I like to suggest 36 caramels in case you have extra dough. xTieghan

      Reply

    1. Hey Cassidy,
      You can use an equal amount of GF flour. I hope you love this recipe, please let me know if you give it a try! xTieghan

      Reply

    2. I have made this recipe GF almost every time! They turn out amazing as long as you chill the dough long enough.

      Reply

  13. Hi Thiegan, these look awesome, but do you think they’d work without the caramel chocolate inside? If yes, do i still need to chill the dough you think?
    Thank you ❤️

    Reply

    2. Hi Luc,
      Sure, I don’t see why not, yes I would still chill the dough. I hope you love the recipe, please let me know if you give it a try! xTieghan

      Reply

  14. Recipe calls for baking soda but when I click on the cocoa you used, it appears it’s dutch process, which typically requires baking powder for a reaction. Can you clarify please?

    Happy Thanksgiving!

    Reply

    1. Hi Stefanie,
      Please follow the recipe as instructed, no baking powder is needed here. Please let me know if you give it a try! xTieghan

      Reply