Crazy for Crust

Aug 17

Rolo Chocolate Chip Cookie Cups

Some days you just need a cookie. Some days you need 5 dozen.

Some days you also want chocolate and caramel. Those are the days you want these cookies: Rolo Chocolate Chip Cookie Cups.

Melty caramel, anyone?

Rolo Chocoloate Chip Cookie Cups - perfect homemade cookies and melty Rolos!

When Jordan was about 1, she started talking. At some point that year, we realized she thought her name was You.

Me (to Jordan): Do you want a cracker?

Jordan: No, you.

Me: You want me to have a cracker?

Jordan: No, YOU.

Me: Okay, I’ll have a cracker.

Jordan: NO YOU!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!

About the time the decibel level of the last “you” broke the windows, we realized she thought her name was You.

Moral of the story? Use your child’s name during their first year. Don’t just say “Do you want a cracker?” or “You are so cute” or “I love you!”

Believe me, they’re listening.


Want to know one of my only #momwin moments of Jordan’s food-related childhood? She was 13 months old the first time she had a cookie. We were at a restaurant at a mom’s group play group and they gave all the kids free cookies. I remarked this would be her first and everyone gasped.

I’m kind of glad I have that moment. Because yesterday she ate almost an entire bag of Jolly Rancher’s before I realized I’d said “yes” about 37 too many times.

If I let her, she’d eat this whole batch of Rolo Chocolate Chip Cookie Cups. I know I would!

Rolo Chocoloate Chip Cookie Cups - perfect homemade cookies and melty Rolos!

Like I said, sometimes you feel like a cookie. Last week I sure did. #longstory

And what’s better than a cookie? A cookie cup.

What’s better than a cookie cup? A cookie cup with a Rolo on top.

These are like blossom cookies but they’re made in mini muffin pans and you can press your favorite candy on top. They’re pretty much my favorite way to eat chocolate chip cookies.

This chocolate chip cookie base is my favorite recipe. I used it to make bakery style XL chocolate chip cookies, chocolate chip cookie cupcakes, toffee chocolate chip cookies, and orange chocolate chip cookies. It’s a recipe that I’ve always gotten rave reviews about, so why change a thing?

Except this time I did change something: I didn’t brown the butter. Forgive me? I was doing approximately 1,342 other things that same day (including a visit to the Apple Store, my first of two) and didn’t take the step. But you know what? It didn’t matter. The cookie cups are amazing with just melted butter.

Melted butter is my key to the perfect chocolate chip cookie. Melted butter and both granulated and brown sugar, that is. When you add the sugars to the warm butter, the cookie gets a caramelized taste. I’ve never been able to replicate it with softened butter.

Beware though, because this recipe uses melted butter you must chill it. Since the cookies are baked in mini muffin pans, however, the chilling time is cut drastically. That’s why I love baking cookies in mini muffin pans. No need to worry about spreading!

When they come out of the oven and are still hot, you press a Rolo on top. Let everything cool completely, then remove the cookies from the muffin pans. If you store these at room temperature, the Rolos stay soft. Soft and gooey Rolos are a good thing.

Rolo Chocoloate Chip Cookie Cups - perfect homemade cookies and melty Rolos!

Especially in chocolate chip cookie cups!

Rolo Chocolate Chip Cookie Cups

Yield: 5 dozen

The perfect chocolate chip cookie recipe is made in a mini muffin pan and then the hot cookie is topped with a Rolo for a melty caramel cookie cup!


  • 2 sticks butter, melted
  • 3/4 cup granulated sugar
  • 1 cup light brown sugar
  • 2 large eggs
  • 1 tablespoon pure vanilla extract
  • 1 teaspoon baking soda
  • 3 1/4 cups all-purpose flour
  • 1/4 teaspoon salt
  • 1 1/2 cup mini chocolate chips
  • 60 Rolo candies, unwrapped (from about 2-12 ounce packages)


  1. Pour butter into an electric mixer fitted with paddle attachment. While still hot, add both sugars and mix on low until combined. Let sit to cool for a few minutes.
  2. While butter mixture is cooling, combine flour, baking soda, and salt in a medium bowl. Stir and set aside.
  3. Turn mixer (with butter mixture bowl attached) on low. Add eggs, one at a time, mixing completely. Mix in vanilla extract. Add flour mixture to the wet ingredients and mix until combined. Stir in chocolate chips.
  4. Spray mini muffin pans with nonstick cookie spray (I like the kind with flour for these). Scoop 1-1 1/2 tablespoons of dough into each cavity. Chill the pans for at least 1 hour.
  5. Preheat oven to 350°F. Bake cookie cups for about 9-11 minutes (the outside will start to turn a golden color when done).
  6. When the cookie cups come out of the oven, press one Rolo into the center of each. Let cool completely in pans before removing (let the Rolo re-harden or it will collapse). Cookies should pop out easily with the aid of a knife.
  7. Store in an airtight container for up to 4 days or freeze for up to 1 month.

Chocolate Chip Cookie Cake – top with your favorite candy!

Harvest Chocolate Chip Cookie Cake (3 of 10)w

Bakery Style Chocolate Chip Cookies

bakery-style-chocolate-chip-cookies (2 of 6)w

Easy Turtle Chocolate Chip Cookies

chocolate chip turtle cookies

Easy 2 ingredient Junior Mint Chocolate Chip Cookies

Junior Mint Chocolate Chip Cookie Cups (4 of 7)w

Sweets from friends:
Strawberry Sugar Cookie Cups by Julie’s Eats and Treats
Salted Caramel Chocolate Chip Cookie Cups by Diethood
Cheesecake Caramel Pumpkin Cookie Cups by Something Swanky

62 Responses to “Rolo Chocolate Chip Cookie Cups”

  1. Mir posted on August 17, 2014 at 4:30 am (#)

    These look so good! I love using melted butter. So much easier!
    Hilarious about your daughter. My son referred to himself in the third person for two years because we were dumb and said stuff like, “Does Koby want juice?” So yeah, they’re listening!


  2. Danielle @ Chits and Chats and Chocolate posted on August 17, 2014 at 4:54 am (#)

    Everything is cuter when it’s made in a muffin tin! These look like they’d travel really well, good for trips; do they?


  3. Nancy P.@thebittersideofsweet posted on August 17, 2014 at 6:14 am (#)

    This is hilarious! My 2 year old thinks my name is honey because she hears my hubby call me that all of the time! Kids are so cute! Love this recipe!


  4. amanda @ fake ginger posted on August 17, 2014 at 6:15 am (#)

    That’s so funny! I think all my kids thought their name was “no” or “stop” at one point. I love these cookie cups! They look so good!


  5. Kristine @ Kristine's Kitchen posted on August 17, 2014 at 6:39 am (#)

    Mmmm… chocolate and caramel! I’ve got to try making cookie cups, especially with Rolos on top!


  6. Kate @ Diethood posted on August 17, 2014 at 7:50 am (#)

    LOL!!! 😀 I LOVE THAT! I did the opposite… I would say, “Does Ana want a cracker?” (said in a cutsie, very annoying voice)… and when she started to talk, she would say, “Ana wants a cracker”, “Ana wants popsicles”, etc… and this continued for about 2 years! I think your way is better!. :-) Now that I talked your ear off, can I have a batch (or 5) of the rolo-amazingness before me?!? 😀

    Thank YOUUUU for the link love!


  7. Averie @ Averie Cooks posted on August 17, 2014 at 7:58 am (#)

    That cross-section shot with the Rolo melty and gooey…. PERFECTION! Love that! Pinned of course. And thank god you used Rolos and I didn’t…I have a cookie cups post this week I think? or next? I can’t remember, I prescheduled it b/c I’m on vacay :) I used a hunk of dark chocolate. Love your Rolo idea!


    • Dorothy Kern replied on August 17th, 2014 at 1:42 pm

      LOL, we’ve synced. It’s a wonder the internet isn’t awash with all the same things between you, me, Sally, Ashton, and everyone else. Have a fun vacation!!


  8. Lisa | Sweet 2 Eat Baking posted on August 17, 2014 at 8:05 am (#)

    Too funny Jordan thought her name was you. And I was pretty much the same with treats with all 3 of my kidlets. The first time all 3 of them ever tried cake was on their 1st birthdays. 😆 That’s when I pretty much realised I was in for it from that day forward.

    I’ve never tried cookie cups yet. Don’t faint – I know, I know. But that awesome caramelness oozing out is calling me now. If I were to make some (which will be soon hopefully), it’ll be these.


    • Dorothy Kern replied on August 17th, 2014 at 6:39 pm

      Yes, the first birthday. And then it was just downhill from there… ha!


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  10. Gayle @ Pumpkin 'N Spice posted on August 17, 2014 at 10:01 am (#)

    I think I need a cookie everyday! Especially these cookies, Dorothy! Love the rolo in the middle!


  11. Emily @ Life on Food posted on August 17, 2014 at 12:22 pm (#)

    I always need a cookie! I would totally eat the whole batch!! These are fantastic!


  12. Anna @ Crunchy Creamy Sweet posted on August 17, 2014 at 2:47 pm (#)

    Ooo! Rolos! I love Rolos! Especially in cookies! These cookie cups look so good, Dorothy! Pinned!


    • Dorothy Kern replied on August 17th, 2014 at 6:38 pm

      Thanks for the pin Anna!


  13. Laurie F. posted on August 17, 2014 at 5:04 pm (#)

    I love your cookie-in-a-cup idea! And how funny, about Jordan! My daughter had no sweets until she was almost 3 years old, and when she was 2 I used to get compliments from women at the grocery store check stand (“she’s not asking for candy!” – little did they know that she didn’t know what it was. I miss those days!)


    • Dorothy Kern replied on August 17th, 2014 at 6:38 pm

      I miss them too!! She was 1 before she had any sugar. I’ve made up for it in spades… :/


  14. Mom posted on August 17, 2014 at 6:01 pm (#)

    These look really yummy, Kiddo. Wish I had some now.


  15. Kayle (The Cooking Actress) posted on August 17, 2014 at 6:27 pm (#)

    bahahaa that’s so cute that Jordan thought her name was “You”!!

    and I lovelovelove these cookie cups-the texture is major and omg melty caramel!


    • Dorothy Kern replied on August 17th, 2014 at 6:37 pm

      Right? Melty caramel should be a food group.


  16. Frankencookie posted on August 17, 2014 at 6:27 pm (#)

    Just inject sugar into your veins and get the rush over with.


  17. Stephanie @ Back For Seconds posted on August 17, 2014 at 7:25 pm (#)

    Haha! Kids are so funny :)
    These look incredible. That gooey caramel, ahhhh!


  18. Krystle(Baking Beauty) posted on August 17, 2014 at 7:56 pm (#)

    I love trying new varieties of chocolate chip cookies. Love that you threw candy in these ones. Today is totally an I need 5 dozen day!


  19. Jess @ Sweet Menu posted on August 18, 2014 at 2:25 am (#)

    I have never made or eaten a cookie cup before but that looks insanely goooood! I must try! And I just love rolos!


  20. Julie @ Julie's Eats & Treats posted on August 18, 2014 at 1:01 pm (#)

    Ohhhh did you really just stuff a Rolo in the middle of a cookie?! Brilliance! Thanks for the link love too dear!


  21. Heather @ Shards of Lavender posted on August 18, 2014 at 4:08 pm (#)

    I love that you used melted butter for these cookie cups; reminds me of blondies. In my opinion, melty caramel is always welcome, especially when it has chocolate and a cookie wrapped around it!


  22. Erin @ Making Memories posted on August 18, 2014 at 7:02 pm (#)

    Oh my gosh! Yum, yum and more yum! I’ll take the 5 dozen please!


  23. Kelly - Life made sweeter posted on August 19, 2014 at 10:25 am (#)

    Hehe, loved this story. My son thought our names were “you” “honey” and “boo” since that’s what my husband and I call each other. These cookie cups look incredible! I’m dying over all that melty gooey caramel inside – just gorgeous! Pinning!


  24. Sharon @ What The Fork Food Blog posted on August 19, 2014 at 11:07 am (#)

    I made rolo cookie cups a few months ago with peanut butter cookies. The chocolate chip version looks fab!


  25. Mary Frances posted on August 19, 2014 at 11:34 am (#)

    That is awesome. I don’t think we’ve had a kiddo think their name was “you” (it makes for a fantastic story though!) but we’ve definitely had our fair share of three too many cookie episodes. This caramel and chocolate combo is too good … I would forget anything resembling self control around these. That gooey middle, whew, so so good!


  26. Hayley @ The Domestic Rebel posted on August 19, 2014 at 3:14 pm (#)

    Dude, I always forget about Rolos and then remember, OH YEAH, THESE ARE FREAKIN’ AWESOME! I used Rolos in a recipe I made yesterday and have been snacking on the rest of the bag since. Oops :) better save some for these cups!


  27. Kristyn posted on August 21, 2014 at 9:07 am (#)

    Cookies AND Rolos?? Sounds like a great combo to me!!


  28. Amy @ Amy's Healthy Baking posted on August 21, 2014 at 7:20 pm (#)

    Ohmygoodness, that’s just the cutest story about Jordan’s “you!” Seriously. :) My brother and his best friend stopped by to visit me one time after they saw his best friend’s sister’s new baby, and apparently my brother talks to babies the same way as he talks to dogs. But knowing how I talk to our dog (“Is Twinkie a good girl? Does Twinkie want to go for a walk?”), that’s probably a good thing! 😉


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  30. Martha posted on August 27, 2014 at 4:13 am (#)

    Our favorite is to use Reese’s mini cups in these-they are a Xmas favorite.


  31. Jocelyn@Brucrewlife posted on August 28, 2014 at 12:05 am (#)

    The story about Jordan is too cute!! 😉 It definitely brings to mind a lot of sweet little things my kids used to say/do! And these little cookie cups need to get in my belly pronto!! Yum!!


  32. Kim Miller posted on August 29, 2014 at 5:15 am (#)

    I wonder how these would taste with a big glob of your homemade Dulce De Leche in the middle instead of a rolo….I happen to have three jars (started with 6….don’t ask where the other 3 went ;)) in the fridge and I’m thinking the taste would be awesome!


  33. Aine O'Flaherty posted on September 8, 2014 at 8:04 am (#)

    Thanks for such an amazing idea. I am in the UK but ill convert all the measurements.
    I was wondering about them being in the pan for an hour prior to baking , is this correct ??
    How do have time to bake such delicious things & be a mom .. well done


  34. Aine O'Flaherty posted on September 8, 2014 at 8:05 am (#)

    Thanks for such an amazing idea. I am in the UK but ill convert all the measurements.
    I was wondering about them being in the pan for an hour prior to baking , is this correct ??
    How do have time to bake such delicious things & be a mom .. well done


    • Dorothy Kern replied on September 8th, 2014 at 6:48 pm

      You chill them to let the dough rest – makes them taste better!


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  36. Pat Donnelly posted on September 11, 2014 at 4:30 am (#)

    Also good with either a chocolate kiss or a peanut butter cup the middle Yummy!


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  38. Pamela Terhune posted on October 7, 2014 at 12:22 pm (#)

    Hi Dorothy, Love your site! I have a question. Can I use break and bake cookies instead? I have 2 packs of cookies in the fridge AND Rolos. Just wondering if this way would work too. Thank you! xoxo


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  43. Barbara Lohff posted on November 19, 2014 at 1:30 pm (#)

    Do you really use 1 tablespoon of vanilla extract? Not 1 teaspoon?
    They look awesome!


    • Dorothy Kern replied on November 19th, 2014 at 4:00 pm

      Yes, 1 tablespoon! I love vanilla, so I use a lot. :)


  44. Claudia posted on December 2, 2014 at 12:52 pm (#)

    Hi. What is the measurement for 2 sticks of butter


  45. kristin posted on December 14, 2014 at 3:56 pm (#)

    What is the best way to cook these quickest without having to wait an hour between every set.  I only have 2 12cup pans so I have to wait an 1hr every time I put new dough in?  Also do you scoop a rounded tablespoon in tin or dI you press it in?  Wasn’t ssureif you make a thumbprint to put roll in at end or just cook like a muffin then push in after?


    • Dorothy Kern replied on December 14th, 2014 at 6:45 pm

      I use a 1-tablespoon cookie scoop, drop it in the tin, then push it down a little. You can scoop all the balls of dough onto a cookie sheet, cover, chill, then pop them in the tins as you go!


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  47. Laura posted on February 15, 2015 at 10:29 am (#)

    Hi! Can I put baking cups in the muffin pan? Or would this affect the way the cookies bake!?

    Thanks in advance! :)


  48. Myura Krouch posted on February 22, 2015 at 7:13 pm (#)

    Do you HAVE to chill them?


    • Dorothy Kern replied on February 23rd, 2015 at 10:18 am

      Since they’re in mini muffin pans instead of on cookie sheets, probably not. But I haven’t tried it, so let me know!


  49. Myura Krouch posted on February 23, 2015 at 10:19 am (#)

    They cane out really good! Everyone loved them!


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