These Rolo Cookie Cups are chocolate chip cookies baked into cups, filled with delicious chocolatey caramelly Rolos.  

Can I just have all my cookies like this? Forever! Served in cup form? 

This is one of my favourite cookie recipes ever! I mean just look at these cookies!  

Rolo Cookie Cups  

Okay, alerady on my blog I have Mini Cookies. I also have a Giant Cookie Recipe on my blog too. If you haven’t already guessed these cookies are baked into cups and are filled with Rolos. I baked the cookies into a muffin tin so they are cupcake shaped.  

These cookie are so easy to make. I used the paddle attachment on my mixer to whip up the cookie dough and because these are cooked in a muffin tray they don’t spread!  

The easiest way to stop the cookies from sticking is to use cake release spray on the muffin tray. You could also use butter or greaseproof paper.  

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I started by mixing together the butter and sugar until it was lovely and creamy and fluffy. Next I added in the remaining ingredients and mixed until it was a lovely smooth cookie dough.  

This cookie dough does contain an egg so it isn’t safe to eat raw. If you would like to eat is raw then just replace the egg was milk adding 1tbsp of milk at a time mixing between each addition until the dough comes together.  

I rolled the dough into equal sized balls and placed them in the muffin tin. Next, using the floured end of a rolling pin I pressed the cookie dough into each cup leaving a hole in the middle.  

Filling the Cookie Cups

I filled the hole with as many rolos as I could possibly fit in the centre. I used a combination of large rolos and mini rolos. Again, you can use either or both.  

 I then rolled the remaking dough into 12 small balls and place them on top of my cookie cups. I pressed them flat into place on top of my cookie cups and baked into the oven.  

When you are pressing the lids onto the top of your cups, you make sure there are no gaps. You don’t want the chocolatey caramelly rolos to seep out or you will end up with a sticky mess.  

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Equipment  

Muffin Tray   

Mixing Bowl  

Spatula

Scales

Rolling Pin

Ingredients  

Unsalted Butter – You can use either unsalted butter or stork in these cookies. The butter in the recipe is what makes the cookies lovely and soft and chewy. If you want a crunchier cookie just remove some of the butter.  

Light Brown sugar – The light brown sugar gives the cookies an almost toffee flavour. Brown sugar also helps retain moisture making the cookies softer. If you want a crispier cookie you could use granulated sugar instead. Or you could use a combination of the two.  

Plain Flour – Flour holds the cookie together. In this recipe I used plain flour rather than self-raising. Self-Raising flour makes the cookies cakier and also, I didn’t really want my cookies to rise.  

Eggs – Eggs help binding the cookie together. The egg in this recipe means that the cookie will rise more and spread less. So, you will have a puffier cookie.  

Vanilla Extract – I used Vanilla Extract to flavour the cookies.  

Chocolate Chips – I used white, milk and dark chocolate cookies but you can use one flavour of chocolate or a combination of the three if you would prefer.  

Rolos – Depending on where in the world you live you may not have come across Rolos. They are little chocolate cups filled with caramel. When you bake these inside the cookie cups in the oven the make the most delicious melted chocolate/caramel centre.

Rolo Cookie Cups

Sarah Mark
These Rolo Cookie Cups are chocolate chip cookies baked into cups, filled with delicious chocolatey caramelly Rolos.
5 from 10 votes
Prep Time 30 mins
Cook Time 15 mins
Total Time 45 mins
Servings 12 cookie cups

Ingredients
  

For the Cookie Cups

  • 125 g Unsalted Butter or Stork
  • 150 g Light Brown Sugar
  • 300 g Plain Flour
  • 1 tsp Cornflour
  • 1 Large Egg
  • 1 tsp Vanilla Extract
  • 300 g Chocolate Chips
  • 270 g Rolos (4 x tubes or Rolo and 1 x bag of mini rolos)

Instructions
 

To Make the Cookie Dough Cups

  • Preheat the oven 180C (160C Fan) and grease your muffin tray.  
  • In a large bowl mix together the butter and sugar until it is light, creamy and fluffy.  
  • Add in the flour, cornflour, eggs and vanilla and mix until all the ingredients are incorporated and a dough is formed. Add in the chocolate chips and mix again until they are all evenly distributed.  
  • Remove 260g of cookie dough, you will use this for the lid of your cookie cups. 
  • Split the remaining dough into 12 equal balls and press them into your muffin tin. I found the best way to do this is by using the floured top of a rolling pin.
  • Fill all 12 cookie cups with rolos.
  • Using the remaining 260g of dough, split this into 12 equal smaller balls and place on top of your cookie cups.  
  • Press the lids down to ensure that there is no gaps that your rolos could leak from.  
  • Put your mixture in the oven for 15-17 minutes until they are golden brown.  
  • Leave your cookies to cool in the muffin tray, it makes them easier to get out.

Notes

  • These would be perfect warmed up and served with ice cream. You can heat them in the microwave for a few minutes or pop them back in the oven for a couple of minutes. 

  If you do have any questions about this recipe or any other recipes on my blog you can contact me either by the Facebook message symbol in the bottom right corner of your screen. You can also send me a DM on social media or an email. You can find all my details on the right-hand side of this page. 

34 Comments

  • Aaliyah

    1 October 2020 at 8:33 pm

    5 stars
    Rolos are my favourite! These look amazing, I’m not much of a baker but you make it doing so easy so I think I’ll give them a try! X

    1. aspoonfulofvanilla

      4 October 2020 at 2:00 pm

      Yeess! Do it! I hope you enjoy it when you do make them!

  • Anika

    1 October 2020 at 8:39 pm

    5 stars
    Rolos used to be my favourite sweet treat, I haven’t had them in so long! I love the idea behind this, definitely sounds like a fun recipe I want to try 😍

    Anika | chaptersofmay.com

    1. aspoonfulofvanilla

      4 October 2020 at 1:50 pm

      If you do try it let me know what you think! Rolos are one of my favourite sweets too!

  • Smelly socks and garden peas

    1 October 2020 at 9:20 pm

    I can think of 2 small boys and a grown up one in this house who would love these.

    1. aspoonfulofvanilla

      4 October 2020 at 1:59 pm

      I hope you enjoy them!

  • Nic | Nic’s Adventures & Bakes

    3 October 2020 at 12:08 pm

    5 stars
    Thanks for sharing, these look amazing, perfect for quick dessert 🙂

    Nic | Nic’s Adventures & Bakes

    1. aspoonfulofvanilla

      4 October 2020 at 1:49 pm

      They are super quick and easy to make. Also, they are incredible warmed up with ice cream!

  • Sarah

    28 December 2020 at 7:28 pm

    Delicious- not much of a baker so could you tell me if these are supposed to be like a biscuit – as in crumbly and hard (ish) or soft and like a cake (muffin)

    1. aspoonfulofvanilla

      9 January 2021 at 12:59 pm

      Not a problem. They are a cookie so should have the same taste and texture as one of those just with some chocolate sweets in the centre.

  • Lucy

    16 January 2021 at 4:29 pm

    These Rolo Cookie Cups look delicious Sarah! These are something I haven’t heard of before but they look so tasty! x

    Lucy | http://www.lucymary.co.uk

    1. aspoonfulofvanilla

      22 January 2021 at 10:30 pm

      Thank you! x

  • Jupiter Hadley

    16 January 2021 at 4:45 pm

    5 stars
    Oh wow, these look so simple and yet so good!

    1. aspoonfulofvanilla

      22 January 2021 at 10:30 pm

      Thank you!

  • Karalee Shotola

    1 April 2021 at 10:48 am

    5 stars
    I don’t think I’ve had Rolos before, but these look yummy & I love the idea of making cookie cups in a muffin tin!

    1. aspoonfulofvanilla

      4 April 2021 at 9:33 pm

      You need to try them. They are like little chocolate cups filled with caramel!

  • Eleanor Jones

    1 April 2021 at 10:54 am

    5 stars
    Wow these look amazing, I love rolos and this recipe sounds like a great Easter bake! Thank you for sharing x

    1. aspoonfulofvanilla

      4 April 2021 at 9:34 pm

      Thank you!

  • Alice Myles

    1 April 2021 at 11:02 am

    Oooh these look SO GOOD! I love rolos and I love the idea of baking them in a cup instead of flat!

    1. aspoonfulofvanilla

      4 April 2021 at 9:34 pm

      Yes and then you can add whatever chocolate or filling you love. They are delicious.

  • Jenny in Neverland

    1 April 2021 at 11:05 am

    5 stars
    God I haven’t had rolos in SO LONG! These look so sweet and the perfect little snack to have with a cuppa! x

    1. aspoonfulofvanilla

      4 April 2021 at 9:34 pm

      Oh yes! These would be amazing with a cup of tea!

  • Cristina Rosano

    1 April 2021 at 11:09 am

    I never tried rolos, but love the idea of baking them in a tin, they look amazing! They look so tasty and delicious, for me everything involving chocolate is a must-try! Thanks for sharing x

    1. aspoonfulofvanilla

      4 April 2021 at 9:34 pm

      Thank you!

  • Brooke Ressell

    1 April 2021 at 12:43 pm

    These look so good. I love rolos so you know they’re going to be gooey and delicious.

    1. aspoonfulofvanilla

      4 April 2021 at 9:36 pm

      Yes! They are delicious aren’t they?

  • Tania Vialls

    1 April 2021 at 3:25 pm

    5 stars
    Cookies with ROLO! My kiddos are going to live this. I’ll have to hide a batch for me and hubby. LOL

    1. aspoonfulofvanilla

      4 April 2021 at 9:37 pm

      Hahahaha! I hope you all love it if you do bake them!

  • Della Driscoll

    1 April 2021 at 6:56 pm

    5 stars
    Another recipe where my mouth is watering!! These look amazing, I need to try them – love cookie cups x

    1. aspoonfulofvanilla

      4 April 2021 at 9:38 pm

      Thank you!

  • Alex

    10 April 2021 at 4:57 pm

    Oh wow, I’ve never seen cookies like this before. They look absolutely amazing! I have to invest in a muffin tin and give this a go.

    1. aspoonfulofvanilla

      15 April 2021 at 8:02 pm

      Yesss! I hope you enjoy if you do make theses

  • Headphonesthoughts

    11 April 2021 at 3:17 am

    5 stars
    I don’t believe I have had a rolo before but these looks so delicious and good and easy to make.

    1. aspoonfulofvanilla

      15 April 2021 at 8:24 pm

      What?! Rolos are delicious they are like little Chocolate Cups with a Caramel centre x

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