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Oreo-Stuffed Chocolate Chip Cookies

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Enjoy two of your favorite cookies in one with this soft stuffed cookie recipe! Oreo-stuffed chocolate chip cookies will be a new favorite cookie. Keep extra in the freezer to bake on demand, or make a double batch to share as gifts!

chocolate-drizzled oreo chocolate chip cookies on a serving plate in the background. A single cookie is in the foreground with scattered chocolate chips and oreos in the frame

Big, soft, and unapologetically indulgent, this stuffed chocolate chip cookie recipe is a must. How could they not be? You take one amazing cookie and stuff it with another! Then, add a drizzle of chocolate (because why not?) and you have one fabulous treat guaranteed to bring smiles.

I probably have such a soft spot for these cookies because of their origin story. One day, I needed to bake an extra special treat for some extra special recipients.

You know I’m a firm believer in using what you have around the kitchen to get creative, but supplies were a little low. I had some regular chocolate chips, a package of Oreos, and that was basically it. Well, there were nuts too, but the treats had to be nut-free, so that wasn’t an option. I also wasn’t feeling a trip to the store.

close-up of the just-baked oreo-stuffed chocolate chip cookies on a baking sheet

So, after a little thinking, I decided to stuff an Oreo into a chocolate chip cookie and call it a day! I’m kind of on a stuffed cookie kick anyway. This is neither the first nor the last stuffed cookie recipe you’ll see on this site.

As of the date of publishing, I have a chocolate ganache stuffed cookie recipe, caramel stuffed cookies, and the creme brulee cookies already posted. More to come. 😉

But for now, let’s talk about these chocolate chip cookies…

How do you get these Oreo-stuffed chocolate chip cookies to stay puffy?

This cookie recipe is a little different than my usual because big cookies need a slightly different recipe. You still use the usual flour, sugar, etc, but the ratios need to change. The ratios have to change so that you can bake the cookie for a short enough time that it doesn’t spread too much and flatten, but still long enough that it cooks through.

To accomplish all of this, we make a few tweaks to one of my favorite chocolate chip cookie recipes to get the desired results.

stacked cut cookie to show size

First, the amount of sugar is decreased. The funny thing is, no one even notices in the final cookie! The reason behind this is two-fold. First, you want to decrease browning, which happens to sugar as it bakes. Second, reducing the amount of sugar also reduces the amount of spreading. We want big cookies, yes, but big and puffy, not flat.

Second, we add a little more baking powder and a little less baking soda. Both baking powder and baking soda are leavening agents used to provide lift to baked goods. There are a few differences, and they aren’t interchangeable, but both play a role in this recipe.

We decrease the amount of baking soda, since it begins to work as soon as it’s mixed into the batter. To get the best result from these cookies, you want to bake them cold, so we can’t rely on baking soda to do all the work.

Therefore, we add a little more baking powder than usual. Not too much extra, of course, because baking powder can leave a metallic taste if used in excess.

top view of the surprise inside cookies on a baking sheet - you can only fit about 5 or 6 to allow for good air circulation

Most baking powder sold in stores is “double acting”. This means that the reaction happens in two stages. The first occurs at the time of mixing, like baking soda. The second reaction triggers via heat during baking. Therefore, increasing the amount of baking powder means that we still get a good “lift” in our cookies during baking, even after chilling. Although, I’ve baked these just after mixing and the results have also been wonderful! You just get neater circles after a little chilling time.

A few recipe notes…

These are pretty big cookies! If you notice in the video, I take two medium scoops of cookie dough and place an Oreo between them. To make them slightly smaller, you may use only one and a half medium cookie scoops per Oreo. It’s still plenty of cookie, but not quite as large.

As shown, the cookies weigh almost a quarter-pound each! I weighed them. Without the chocolate drizzle, most are just over 3.5 ounces because I used perfectly level scoops to ensure evenly-sized cookies. Next time, I may add a little dough to get each dough ball to 4 ounces before adding the chocolate drizzle. Yum!

If possible, assemble your oreo-stuffed chocolate chip cookies at least 2 hours before you plan to bake them. Letting the cookies sit in the refrigerator until cold (and up to 2 days!) helps flavor development and final shape.

When you bake, watch the cookies towards the end of the baking time. Overbaked cookies will end up hard, and you don’t want that. You’ll see the slightest sign of browning along the edges of the cookies, and the tops will look set, but not particularly brown. Take them out of the oven, the cookies are ready!

close up of a hand holding an oreo stuffed chocolate chip cookie cut in half.

After removing the cookies from the oven, let them sit on the cookie sheet. I always want to skip this step, but it’s important. With the filling, the cookies need a little extra time to set so they don’t fall apart as you transfer them to a cooling rack. Give the cookies 5 minutes on the sheet before moving them. Wait until they are cool before adding the chocolate drizzle.

Finally, the cookies taste amazing at room temperature. You’d think that a stuffed cookie would be best warm, right? We never found ourselves heating the oreo-stuffed chocolate chip cookies. At least, not unless the cookie are to be a base for a mini ice-cream sundae. If you’re going to be a little extra, why not properly commit?

offset stacked cookie cut in half to show the oreo surprise hidden inside!

Happy baking, darlings!

top view of the surprise inside cookies on a baking sheet - you can only fit about 5 or 6 to allow for good air circulation

Oreo-Stuffed Chocolate Chip Cookies

Yield: 14 cookies
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes

Enjoy two of your favorite cookies in one with this soft stuffed cookie recipe! Oreo-stuffed chocolate chip cookies will be a new favorite cookie!

Ingredients

  • 12 tablespoons unsalted butter, softened
  • 1 cup light brown sugar (packed)
  • 1/3 cup powdered sugar
  • 2 large eggs
  • 2 1/2 cups all-purpose flour
  • 1 teaspoon kosher salt
  • 1 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 2 tablespoons cornstarch
  • 2 teaspoons vanilla extract
  • 2 cups chocolate chips (see notes)
  • 14 Oreo cookies, or other chocolate sandwich cookie
  • 1/2 cup chocolate candy coating and sprinkles (optional)

Instructions

  1. Line two baking sheets with parchment paper. Set aside.
  2. In another mixing bowl, sift together the flour, salt, baking powder, baking soda, and cornstarch.
  3. In the bowl of your stand mixer fitted with the paddle attachment, or using a hand mixer and a large mixing bowl, cream together the butter and sugars until light and very fluffy, somewhere between 3-5 minutes (see notes).
  4. Add the eggs, one at a time. Scrape the sides of the bowl after each addition. Stir in the vanilla extract.
  5. Stir in the dry ingredients in 3 batches, scraping the sides of the bowl after each. You want to make sure all the dry ingredients are incorporated and no flour is left at the bottom of the bowl.
  6. Using your rubber spatula, fold in the chocolate chips.
  7. Use a medium cookie scoop to portion out the cookies on a baking sheet.
  8. Take one ball of cookie dough and flatten it slightly. Place an Oreo in the center. Flatten another ball of cookie dough and place it on top of the Oreo. Shape the chocolate chip cookie dough into a disc. Place on the cookie sheet once again. Continue until all the Oreos and cookie dough mounds have been used.
  9. Cover the cookies loosely with plastic wrap and refrigerate while you preheat your oven. You may shape the cookies and refrigerate up to 2 days before baking. If you'd like to prepare them further in advance, Freeze at this point. Once the cookies are frozen solid (about 2 hours), transfer to an airtight container and keep in the freezer for up to 3 months.
  10. When you are ready to bake, preheat your oven to 375 degrees Fahrenheit. Place the cookies on parchment paper-lined baking sheets, leaving 2 inches of space between each cookie.
  11. Bake the cookies for 13-15 minutes (see notes). When you see a very light golden color along the edges of the cookies, the baking time is complete.
  12. Allow the cookies to rest on the sheets for 5 minutes before transferring to a wire rack to cool.
  13. If you are adding the chocolate drizzle: Once the cookies are completely cool, place them on a sheet of parchment or wax paper. Melt the candy coating in the microwave for one minute at 50% power. Stir, then heat for additional 30-second intervals as needed until smooth. Use a piping bag or a fork to drizzle the cookies with the chocolate. Allow the chocolate to set before storing the cookies. If you'd like to add sprinkles to decorate, add them now.
  14. Store the completely cooled cookies in an airtight container at room temperature for up to a week.

Notes

  • You'll be beating the sugar and butter a bit longer than usual because you want to incorporate air into the batter. This helps the cookies maintain a good texture, even when each one has a good amount of dough.
  • Chocolate chips are a personal preference. A semi-sweet or bittersweet is classic, or mix up half semisweet and half dark or milk. 2 cups is a pretty good amount of chips, but I believe you should measure based on what you feel looks right to you.
  • Refrigerated cookies will bake in 13-15 minutes. If you are baking the cookies from frozen, you'll need to add 2-3 minutes to the baking time.

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