Rolo Stuffed Chocolate Chip Cookies – An Indulgent Snack

by Erin, The $5 Dinner Mom on March 23, 2011

rolo stuffed cookies 3

I’ve just got to get this out of my system.

Ever since I saw these Oreo Stuffed Chocolate Chip Cookies over at Picky Palate, I’ve been wanting to try something similar. I have a little thing for chocolate chip cookies. And by little, I mean big. And by big, I mean huge. And by huge, I mean…

You get the picture.

After making these, I’m really not sure that chocolate chip cookies will ever be the same again. I am not sure I’ll ever be able to make unstuffed cookies again!

The key with these…

You have to let them cool to just the right temperature.  Still a bit warm, but cool enough for the caramel to have started to harden.  But only just a little bit.

And if you get it at just the right time, you take a bite…and as you pull the cookie away, a long string of caramel forms and you have to catch it!

It’s a moment of ooey, gooey stuffed cookie perfection.

I sure hope you can recreate that moment!

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Rolo Stuffed Chocolate Chip Cookies

Inspired by Oreo Stuffed Chocolate Chip Cookies


  • 2 1/2 cups flour
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1 cup butter or margarine
  • 3/4 cup sugar
  • 3/4 cup brown sugar
  • 1 tsp vanilla
  • 2 eggs
  • 2 cups chocolate chips
  • Enough Rolos for each cookie, about 18


  • In a mixing bowl, whisk together the flour, baking soda and salt.
  • In a stand mixer or mixing bowl, beat together the butter/margarine and the 2 sugars. Add in the vanilla. Beat in the eggs, 1 at a time, until smooth. Scrape down the sides if necessary.
  • Add the dry ingredients and mix on low speed, until batter forms.
  • Fold in the chocolate chips.
  • Flatten the Rolos, using a potato masher, or the bottom of a measuring cup.
  • Form the cookies by placing dough on top and on bottom of the flattened Rolos. Place on cookie sheet, or Silpat baking mat, and bake at 350 for 9-11 minutes, or until begin to golden.
  • Let cool slightly before serving. Makes 18-24, depending on how much dough you use for each cookie.

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{ 15 comments… read them below or add one }

Tammy March 23, 2011 at 2:51 pm

Thanks! Just what I needed on a day I’m on a clear-liquids diet! =) Hee hee ~ after my procedure tomorrow, though ~ these are on the “to do list” ~ they look fabulous!!! =)


Linda March 23, 2011 at 3:23 pm

Oh my….. these look just amazing ! thanks Erin for the lovely pictures. I will have to try this, as long as I don’t eat all the Rolo’s before.


Tammy Lou March 23, 2011 at 5:17 pm

This sounds like a great idea! I love rolos but when they’re tough to chew when they’re cold (I always worry that I will lose a crown) so this would be perfect!


Angela G March 23, 2011 at 7:19 pm

OMG. Too yummy looking. And to think, I was ahem I mean I am going off chocolate for two weeks. Saved by the fact that I have NO Rolos in my house. Phew.


Laurie March 23, 2011 at 8:42 pm

I gave up chocolate (and all sweets!) for Lent. I am soooooooo planning to make these to enjoy the day after Easter . . . Easter Day is dedicated to Cadbury Eggs alone!


TheGourmetCoffeeGuy March 23, 2011 at 11:24 pm

A great recipe for a day of delicious self-indulgence. Very nice photo.


Food on the Table March 23, 2011 at 11:39 pm

Ooh! Reminds me of a recipe I saw on a blog a few days ago. Get this: cake ball-stuffed chocolate chip cookies. Basically, any sort of dessert-stuffed dessert is a winner in my book.

Thanks for sharing this!


Tricia H March 24, 2011 at 12:40 pm

Oh my!!!!


Crystal's Cozy Kitchen March 24, 2011 at 1:38 pm

I made cookies stuffed with rolos as well, they were absolutely delicious! However, I did not flatten them and they turned out great.


The Marketeer March 28, 2011 at 4:55 pm

Those look good enough to sell at a markup! …Or eat.

Cheers! The Marketeer.


Audrey April 3, 2011 at 2:22 pm

These cookies look amazing! I couldn’t wait to try them, but had no Rolo…so, I dug around to find something else to stuff them with. I had some chocolate cheesecake so I stuffed the cookies with about 1/2 tsp of that instead. Awesome!!!! Thank you for the inspiration and for the delicious recipe!


Cathy Cordero December 30, 2011 at 11:02 pm

So how DO you get your cookies to not spread all over the place?? I tried making these tonight, followed your directions exactly and they spread and then fell apart because they were so thin even after cooling for a bit.


Erin Motz February 8, 2012 at 9:41 pm

I just discovered your blog and I love your ideas. :-) I have to say, WOW! These look incredible! Bookmarking this for later… and by “later” I mean in like 15 minutes, haha.


Lisa Moore March 1, 2012 at 12:07 pm

At a place called Truffle Berries in town they have these BUT they’ve had Ruffles potato chips added to them and are called PMS Cookies. Oh, they are awesome!


Stephanie July 7, 2012 at 8:56 am

Just now discovering your blog — so many great new recipes to try out. Rolo cookies are a holiday staple in my family. We make them in a chocolate cookie, dusted with chopped pecans and sugar. Delish. You can also just roll the unflattened Rolo into the cookie dough ball and they’ll turn out great. I gotta give these chocolate chip cookie ones a try some time soon!


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