Crazy for Crust

Aug 15

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

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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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60 Responses to “Rolo Stuffed Oatmeal Cookies {Back-to-School Printable}”

  1. Averie @ Averie Cooks posted on August 15, 2012 at 6:16 pm (#)

    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. Trish - Sweetology101 posted on August 15, 2012 at 6:39 pm (#)

    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. Trish - Sweetology101 posted on August 15, 2012 at 6:40 pm (#)

    This comment has been removed by the author.


  4. Jocelyn posted on August 15, 2012 at 8:28 pm (#)

    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. Kristin posted on August 15, 2012 at 8:36 pm (#)

    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. keri @ shaken together posted on August 16, 2012 at 1:24 am (#)

    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. posted on August 16, 2012 at 3:50 am (#)

    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. The Cooking Actress posted on August 16, 2012 at 4:28 am (#)

    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. Sue @ Cakeballs, cookies and more posted on August 16, 2012 at 4:30 am (#)

    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. Aimee @ ShugarySweets posted on August 16, 2012 at 4:51 am (#)

    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. Jessica@AKitchenAddiction posted on August 16, 2012 at 5:04 am (#)

    I would love to be a teacher and receive these! :) These cookies are wonderful!


  12. Hayley @ The Domestic Rebel posted on August 16, 2012 at 7:42 am (#)

    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. Dip It In Chocolate posted on August 16, 2012 at 10:00 am (#)

    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. sally @ sallys baking addiction posted on August 16, 2012 at 11:29 am (#)

    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. Chung-Ah | Damn Delicious posted on August 16, 2012 at 11:36 am (#)

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


  16. The Pastry Chef posted on August 16, 2012 at 12:10 pm (#)

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


  17. Christina @ Oven Adventures posted on August 16, 2012 at 2:02 pm (#)

    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. Ellen posted on August 16, 2012 at 4:00 pm (#)

    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. Lisa {Sweet 2 Eat Baking} posted on August 16, 2012 at 5:11 pm (#)

    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. Meg @ Sweet Twist posted on August 16, 2012 at 6:27 pm (#)

    Can I lie and say I am a teacher so I get some. :-)


  21. Back for Seconds posted on August 16, 2012 at 8:06 pm (#)

    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. Heather Kinnaird posted on August 16, 2012 at 9:11 pm (#)

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


  23. Winnie posted on August 17, 2012 at 1:15 am (#)

    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. Me And My Sweets posted on August 17, 2012 at 5:59 am (#)

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


  25. A Proverbs 31 Wife posted on August 17, 2012 at 8:46 am (#)

    I’m drooling! Oh and it’s so pinned for later :)


  26. Sweet Bella Roos posted on August 17, 2012 at 11:40 am (#)

    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. Ang posted on August 17, 2012 at 1:17 pm (#)

    oh my – so delicious – love this!!


  28. Nicole {WonkyWonderful} posted on August 17, 2012 at 11:34 pm (#)

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


  29. Anonymous posted on August 18, 2012 at 8:42 am (#)

    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. Ashley @ Kitchen Meets Girl posted on August 18, 2012 at 8:48 pm (#)

    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. Ang posted on August 20, 2012 at 8:15 am (#)

    we tried these this weekend – oh so yummy! :)


  32. Something Swanky posted on August 20, 2012 at 7:44 pm (#)

    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. Erin posted on August 21, 2012 at 8:08 am (#)

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


  34. Trish posted on August 22, 2012 at 3:09 pm (#)

    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. Six Sisters posted on August 23, 2012 at 9:48 am (#)

    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. Dawn @ DJ's SUgar Shack posted on August 25, 2012 at 1:12 pm (#)

    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. Kaylee posted on August 25, 2012 at 7:01 pm (#)

    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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  40. nicole j posted on July 28, 2013 at 12:56 pm (#)

    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?


    • Dorothy Kern replied on July 29th, 2013 at 7:36 am

      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. Jen Nikolaus posted on August 7, 2013 at 4:42 pm (#)

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


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