Inside-Out Twix Cookies

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Is it really Friday already? Wowzers!

Inside-Out Twix Cookies. Well, we’ve all obviously survived the first month of the year, but clearly I’m late to the January health-fads party. Sorry, my mind is still stuck in holiday baking. Not that it makes it any better, but this is actually the run-off of my enthusiasm for baking during the holidays (plus every other time of year too if we’re gonna be honest here). I just didn’t have time to share everything that I made in December. But I’ll be posting the more diet-friendly things soon, for reals.

Inside-Out Twix Cookies (5) You know what I’m thinking these would be perfect for?….uh huh, Superbowl 2016! Oh wait, I don’t even like football…but I’m all for the football food, guys. These are excellent tailgating material, truth I speak.

Inside-Out Twix Cookies (3) I’m going to be straight with you though, these cookies can get really messy just so you know. I’ve had some complaints from readers recently on some similar recipes that they didn’t come out perfect so I want you all to be forewarned that you are pretty much guaranteed to have at least one oozer in each batch, at least. We’re talking melty chocolate and caramel meets real life baking, hello, there’s always going to be a little messiness involved. The amount of not-so perfect cookies will depend on what you choose to stuff them with. Since I used homemade caramels they were a little extra runny and melty but if you use store-bought ones they should hold up better because there are things added to those to help stabilize the chocolate.

Inside-Out Twix Cookies (2) Whichever you choose, I think any amount of trial and error is worth it cuz these are amazing. Seriously, slam-dunk/show-stopping/crowd-raging madness here! You just have to try em!

Inside-Out Twix Cookies (4) Ok, clearly I’m obsessed with stuffing cookies as of late. In recent months if you haven’t noticed I’ve made these and these and these…. Hey, It’s just really hard to go back to plain cookies once you’ve started down the road of stuffing them with yummy stuff. The exception being when you’re to lazy to put in an extra step, but when you’ve got the time, it’s so worth it. Inside-Out Twix Cookies (6) My mom calls them sugar baby cookies because the texture that the homemade caramels get when you bake them in the dough is such a similar texture to sugar babies candy and she used to love those. And speaking of candy, there aren’t actually twix bars in these, but rather, they were inspired by a twix but in reverse. The chocolate is on the inside while the shorbread-ish cookie in on the outside. Get it?

Inside-Out Twix Cookies (7) So remember what I said about these being potentially messy. Please don’t expect picture perfect cookies every time or your setting yourself up for disappointment. By the way though, the stuff that runs out of the cookies is still very edible (wink wink).

So I hope you had a great week and are planning a fun weekend. Happy friday peeps!

Inside-Out Twix Cookies

Prep Time: 35 minutes

Cook Time: 25 minutes

Total Time: 1 hour

Yield: about 36 cookies


  • 1/2 cup (1 stick) butter, softened
  • 1/2 cup palm oil or organic vegetable shortening
  • 2 cups sugar
  • 1 large egg + 4 yolks
  • 1 teaspoon salt
  • 2 teaspoons vanilla extract
  • 1 teaspoon baking soda
  • 4 cups all purpose flour
  • 36-40 chocolate covered caramels (or rolos)(I used these homemade ones


  1. Cream butter, shortening, and sugar in a large mixing bowl. Beat in egg and yolks, then soda, salt, and vanilla. Add the flour a little at a time and mix until dough is well combined.
  2. roll the dough into 1 inch, about 1 heaping tablespoon each, balls and place them about 2 inches apart on parchment or silicone lined baking sheets. Use you thumb to make a well in the center of each dough ball and stuff a chocolate caramel inside. Squish the sides up a little and roll the dough around it to cover.
  3. Place cookie back on tray and push down slightly then repeat with all cookies. Place the tray in freezer (if it won't fit you can chill the balls on a smaller plate and then put them back on tray) for about 25 minutes to get cold.
  4. While the balls chill, preheat the oven to 350 degrees F (180 C). After 25 minutes, bake for 7 - 9 minutes until the edges are just starting to turn a light tan. Remove and let them cool for at least 5 minutes them loosen from pan and either let them cool completely or eat them while they're still hot and melty!


I should probably also mention that these do not all come out perfectly shaped. Know that some of them will have a little filling ooze out and candy, or possibly even burn, on the pan. What I do is simply let them cool on the tray and cut the cookies away from the runaway filling (p.s. It's really good once it candies like that; baker's privilege!) If some of them get extra flat you can try using a spatula to sort of push the cookie back into shape by scooting in the sides.

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  1. says

    Ugh these look like PERFECTION. They look messy in absolutely the best possible way–I love your mom’s name for them! Sugar baby cookies…it just sounds like you can eat five and it’s fine because they’re baby cookies right? 😉

  2. says

    I’m the same way — I love football food, but I don’t really care for football. Especially if said food is these cookies. They are adorable. I’m diggin the idea of shortbread cookie dough.

    I think that in every batch of cookies, there is a least one weird one, and that’s totally okay. It means you get to eat it yourself and don’t have to share with anyone. Life is made up of imperfections! That being said, do you think there would be less leakage if you froze the caramels twice? (aka freeze them for several hours, wrap in dough, and THEN do step 3?)

  3. Nadja says

    I’m making these the first moment I get this week! However, I’m wondering, the second sentence of the first direction mentions adding white chocolate, but that’s not in the ingredient section. How much and what kind?

    • Tori says

      Hi Nadja! I’m so glad you found these and want to try them. That line about white chocolate was a total typo, so sorry. There’s no white chocolate in this dough, although come to think of it, I bet it would be yummy. I took it out of the recipe so thanks for letting me know. Have a great week!

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