Crazy for Crust

Rolo Stuffed Oatmeal Cookies

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Would it surprise any of you to hear that I was a major goody-goody teacher’s pet in school?

I was the wannabe hall monitor.

I once got in trouble for reading in class. Not reading a passed note. Reading a novel. In the fifth grade.

Even though my mom will say I was a terrible teenager, all surly and teenagey, I was a goody-goody even then.

I never snuck out of my house.

I never cut class.

I did other things that shall remain untold. {Hi Mom!} But, in all truthfulness, I was a good girl.

The teacher’s favorite. The one they could always count on to be on time, have her assignment, and not cheat. {There was, in fact, unbeknownst to me, a cheating ring in my sophomore history class that extended from the person behind me copying from my quizzes that wrapped all the way around the room so that the kid in the farthest corner had my answers on his paper.}

So would it surprise you then to know that, as much as I really do love being the Hospitality Committee chairperson and as much as I love doing things for the teachers at Jordan’s school, I want them to like me.

And to me like is done through kindness, aka food. Or, in my universe, dessert.

When I stuffed Rolos inside of peanut butter cookies it was such a huge hit that I knew I had to do it again. Again, stuffing Rolos inside of cookies isn’t new. I’m not the first to do it and I won’t be the last. But today I’m sharing with you new-to-me Rolos stuffed inside of oatmeal cookies.

I love oatmeal cookies. Almost more than any other kind. {Shhh…you won’t tell peanut butter, right?}

These cookies are for the teachers next week. I’m going to put them in their boxes on the first day of school.

{Pssst…they freeze reeealllly well.}

And because I want them to like me a lot, I made tags for the bags. These are “smart cookie” cookies.

Want the tags? So you can make some cookies for your kids’ teachers?

Gotcha covered. For a .pdf copy of this printable, click here.

Now you can be the most popular too. Dessert = Like. It’s just the truth.

Rolo Stuffed Oatmeal Cookies


  • 1 cup butter — softened
  • 1 cup packed brown sugar
  • ½ cup granulated sugar
  • 2 eggs
  • 1 teaspoon vanilla
  • ¾ cup all-purpose flour
  • ¾ cup whole wheat flour
  • 1 teaspoon baking soda
  • 1 teaspoon cinnamon
  • ½ teaspoon salt
  • 3 cups oats — quick-cooking
  • About 40 mini or regular size Rolos — depending on how big you want your cookies


  1. Preheat oven to 350°. Line your baking sheets with parchment paper or silpat liners.
  2. Mix flour, baking soda, cinnamon, and salt in a medium bowl. Set aside.
  3. In the bowl of an electric mixer fitted with the paddle attachment, beat the butter and sugars until creamy. Add the eggs and vanilla and beat well. Add the dry ingredients and mix until combined. Stir in the oats.
  4. Scoop 2 tablespoons of dough onto a cookie sheet. place a Rolo in the center of each scoop and press the dough around the candy to seal. Roll between your palms. Place about 2” apart on the cookie sheet.
  5. Bake 10-12 minutes. Cool five minutes and then remove from pan to cool completely.

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  1. we tried these this weekend – oh so yummy! 🙂

  2. Soooooooo…. I don’t know how to say this, but… I just made practically the exact same cookie.


    And I’ve been so lost in boxes and moving that I hadn’t even been to your blog in days (sorry about that, by the way)!!!! Can you believe that?

    And when I took the first bite of the cookie tonight, I was like, “OOOOOOOMMMMMMMGGGGGG.” And my husband was like, “Oh, that’s your ‘this is a genius recipe’ sound.”

    SOOOOO good, right???

  3. Your cookies look heavenly (of course) and I just love the printable! Thanks so much for sharing it!!!

  4. Yes!!! These look so yummy – I could easily eat 2 or 6 at a time. Thanks so much for sharing at Mom On Timeout!

  5. These Rolo Stuffed Oatmeal cookies look yummy! We appreciate you linking up to our Strut Your Stuff Saturday link party! Please come back again soon! -The Sisters

  6. I love any thing that is stuffed with rolos. Cookies never last long enough to be frozen in my house. Too many cookie monsters lurking about.

  7. Rolo stuffed anything sounds good to me!

    Thanks for sharing at Mealtime Monday! Can’t wait to see what you link up tomorrow night!


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  10. so i am attempting to make the cookies now, and the batter is super gooey and sticking all over my hands and not rolling like batter should. it feels like there is not enough flour, but i know that if i add anymore its all i will be able to taste. what should i do?

    • I’m sorry! I just saw this comment, was off the grid yesterday. Try chilling the dough before rolling. Sometimes the butter just needs to firm up before it’ll roll pretty!

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