Rolo Stuffed Oatmeal Cookies {Back-to-School Printable}

This post may contain affiliate links. For more information, read my disclosure policy.


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.

Did you make this recipe?

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.

All images and text ©. Please do not use my images without prior permission. If you want to republish this recipe, please re-write the recipe in your own words, or link back to this post for the recipe.

Leave a Reply

Your email address will not be published. Required fields are marked *


  1. I love a good oatmeal cookie – they are so delish when made soft ‘n chewy and with Rolo’s in them? Oh yes!

    I was an overzealous, studious, hard-working student. I look back on my childhood and think, gosh, I should have cut class or thrown spit balls, at least once in my life!

  2. Thank you in advance for being the “favorite mom” after I deliver these treats…thanks for the printable as well! Great things as usual!

  3. This comment has been removed by the author.

  4. Ok this brought back repressed memories of me getting in trouble for reading a book…in 5th grade. What are the odds??? And I never did anything bad either!!! I love rolos, and Rolos in oatmeal cookies is awesome!!! The teachers are going to love you tons…just like we do:-)

  5. When are you coming to MY school? We have amazing PTA moms. But none of them blog. Everyone knows that bloggers have the best ideas 🙂

  6. You & I would have been BFFs in 5th grade, Dorothy! Goody goodies of the world unite 😉 Umm and those cookies look insanely good … pinned!!

  7. You can roll a Rolo….ok enough blast from the past commercials!!! I have fond memories of Rolo’s, love them! Great in this cookie, thats for sure!

  8. Lol!! I was totally a good girl/teacher’s pet too! And I got scolded for reading books during class ALL THE TIME! heheheeee

    These cookies look great-anyone would be ecstatic to get some!

  9. I knew it, you are totally the girl that was too nice, and was so perfect;p I was so the same in that I wanted everyone to like me, but I was never great in school, at least I never cheated. And these cookies, they will make you the most popular girl around!

  10. Oh c’mon I’m sure the teachers love you. I bet they fought over who gets Jordan in their class cause they knew “mom” would bring stuff like this in! YUM.

  11. I would love to be a teacher and receive these! 🙂 These cookies are wonderful!

  12. I’m drooling. These cookies look ahmaaaazing. Rolos inside oatmeal cookies?? Hello, deliciousness. PS, those printables are adorable. PPS, I was a goody-goody in high school too, but hopefully no one cheated off my history tests.

  13. Haha, I too was Hermione Granger-esque in school. Treats are definitely my go-to method for making friends 😉 Have you ever read the book The 5 Love Languages? I’m pretty sure they need a sixth language that involves food, because that one is me.

    Hubs just said the other day “Make me a cookie with Rolos!” Maybe I will just make him yours 🙂 Love oatmeal.

  14. The way to people’s hearts is through their tummys! You know I love these Dorothy, because they are reminiscent of your rolo stuffed PB cookies, which I’ve made and remade about 4 times now. Love the little rolo surprise inside. And oatmeal cookies are my favorite – love the chewy + soft texture oats gives 🙂

  15. Oatmeal cookies are my absolute favorite! And add in some rolos and I’m in heaven!!

  16. You just described my school years, lol. Love this idea and I have Cadbury milk chocolate caramels to use for it – pinning!

  17. if i would have known there was cookies involved i would have been a teacher. 😉

    i am so all over Rolo’s in cookies. Fabulous!

  18. Gosh, Dorothy…These looks soooo gooood! I think these just may have to be made at my house and stored in the freezer for my morning coffee. 🙂 Have a great weekend!!

  19. Dorothy, these look absolutely delicious. And you’re totally right, they won’t just like you for this, they’re going to love you. If I were Jordan’s new teacher, we’d be BFFs.! The printables are fantastic and love the smart cookie wording. Do you use a circle punch to cut them out? I need to get me some of those and send my kids teachers some treats.

    P.S. I noticed you typo’d ‘school’ in the title as ‘shool’.Just thought you should know.
    Sweet 2 Eat Baking

  20. Can I lie and say I am a teacher so I get some. 🙂

  21. How did I miss these earlier? You have me wanting cookies in a big way, girl. Jordan’s teachers are super lucky to have you around.

  22. totally stealing your idea! I am a please like me kind of girl:)

  23. I totally love these cookies. I’m not sure I can use Rolos ( we do have them here, but I’ll have to check if they’re kosher for us), but I loooooooove your idea.

  24. WOW! Great combo! They look insanely good:-)

  25. I’m drooling! Oh and it’s so pinned for later 🙂

  26. Too funny– I’m making the same tags for Bella’s teacher. Apparently I missed the memo that we do back to school gifts, so I had to scramble and of course turned to cookies haha!

  27. oh my – so delicious – love this!!

  28. Yum – I never would’ve thought of this combination … but I’m sure they are amazing! They certainly look delicious 🙂

  29. I never said that you were a terrible kid…you just didn’t speak more than one word sentences to us for a few years. But I could never complain because you were such a goody goody! Besides, I knew how to make you talk; I just took you shopping! With all the trouble you see teenagers getting into, I couldn’t have asked for a better daughter!
    Love you lots, Mom

  30. Oh my gosh–thank you for this printable!! The timing is perfect–I just signed up to be on the teacher appreciation committee, so these are JUST the thing I need. Also, the cookies sound awesome: rolos and oatmeal are two of my favorite things!

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

  32. 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???

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

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

  35. 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

  36. 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.

  37. Rolo stuffed anything sounds good to me!

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


  38. Pingback: Pumpkin Streusel Muffins | Crazy for Crust

  39. Pingback: Free Printables for Teacher Appreciation Week {If you give a teacher a...} - Crazy for Crust

  40. 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!

  41. These cookies sound amazing!! And that printable is so cute! What a great idea!

  42. Pingback: Soft and Chewy Oatmeal Cookies - Crazy for Crust

Leave a Comment »