Rolos oozing our CookiesMr. Big Flavors says that these Rolo Surprise cookies are his very favorite. I’d like to believe that, but that man is a certified cookie monster.  I’m pretty sure all of the cookies he’s ever eaten have been near favorites. Either way, it’s kind of a tradition that I make them every year for his birthday. It also happened to be around the same time that I signed up for the Great Food Blogger Cookie Swap. The swap is a way for food bloggers around the country to “meet” each other through a dozen of cookies, while also showing off their baking skills. It’s also a great way to raise money for Cookies for Kids’ Cancer! It’s a pretty simple, actually. Bake three dozen cookies and ship them off to three other food bloggers. And, you’ll receive three dozen cookies, too! Who doesn’t love getting mail that’s not a pile of bills or credit card solicitation? Since, the deadline for sending off the cookies to the bloggers and Mr. Big Flavor’s birthday were both in the same week – Rolo Surprise cookies seemed to be the logically, perfect answer. Everybody wins!

Chocolate Cookies filled with rolos

I love cookies that look pretty plain on the outside, but have surprise on the inside! And, caramel is always a surprise I can get behind.  These cookies are perfect right out of the oven, while the Rolos are still gooey and the caramel is dripping when you break the cookie apart.  The cookie itself is very soft, so it’s a great dunker for that morning cup of coffee.

Rolo Surprise Cookies

These cookies do take a bit longer than the average roll and drop cookie, but that’s because you’re stuffing them with a surprise!  My advise is to solicit the kids into unwrapping all of those Rolos, so you can save yourself from having to do all of the hard work. Make the cookies as big or small as you’d like. Just make sure the entire Rolo is covered with cookie dough. If not, you might find that the caramel will leak out during baking. Trust me, cookies just aren’t as pretty when you have to furiously scrape the sticky caramel bottom off of your baking sheet.  If you decide to use the walnuts, they’ll also help prevent the rolo from oozing out of the bottom.

Rolo Filled Chocolate Cookies

Take these Rolo Surprise cookies to your next holiday gathering or ring in the new year with a dozen or two.  They sweet treats won’t last long, especially after people realize they have a hidden caramel center!

Rolo Surprise Cookies

Serves 36
Prep time 30 minutes
Cook time 10 minutes
Total time 40 minutes
Meal type Dessert
Website Let's Dish

Ingredients

  • 1 cup white sugar
  • 1 cup brown sugar
  • 1 cup butter (softened)
  • 1 teaspoon vanilla
  • 2 large eggs
  • 2 1/4 cups flour
  • 3/4 cups cocoa
  • 1 teaspoon baking soda
  • 1 bag rolos (unwrapped)

Optional

  • 1 cup walnuts

Directions

1. Preheat oven to 350 degrees. Use a hand mixer to cream together white sugar, brown sugar, and butter. Add eggs and vanilla. Mix well.
2. In a separate bowl, combine flour, cocoa, and baking soda. Add these dry ingredients to the sugar mixture. Mix well, until all ingredients are combined. Refrigerate for 20 minutes to let dough chill.
3. Shape and roll 1 TBSP of dough around 1 rolo. If using, dip bottom of cookies into chopped walnuts. Place onto baking trays lined with parchment paper. Bake for 8 - 10 minutes. Remove and let cool slightly before serving.

Shared with: Crazy Sweet Tuesday, Recipe Roundup, Full Plate Thursday, Weekend Potluck

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8 Responses to Rolo Surprise Cookies

  1. Flavia says:

    These were delicious, Jenna! Thank you again. It was so much fun “meeting” you through this cookie swap. I am looking forward to staying in touch with you.

  2. Lauren says:

    Oh it was a Rolo! Duh!! Still delish – thank you!

  3. Winnie says:

    Oh Gosh – these look soooooooooooo delicious and tempting

  4. vincent says:

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  5. Miz Helen says:

    Thank you so much for sharing your awesome recipe with Full Plate Thursday. Hope you are having a great day and come back real soon!
    Miz Helen

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