Rolo Stuffed Cookies

For the ultimate chocolate lover, these Rolo Stuffed Cookies are prepared with a rich chocolaty and fudgy base, which is wrapped around a single Rolo candy. When you bite into one of the cookies, milk chocolate and caramel oozes out – sounds indulgent, right? Perfect for Christmastime, when calories don’t count!

I just had to look back into my list of previously published recipes to see if I have ever shared a recipe like these Rolo Stuffed Cookies in the past. Unless you could count cookies like these Apricot Kolaches, these Linzer Cookies, or my Newfoundland Jam Jams, then I guess, I have not. And, they are sandwich cookies anyway; not stuffed.

Since I was quite young, I can remember buying those familiar tubular packages of Rolo candy. I used to consider them a chocolate bar, but I think they fall under the candy category. Either way, they’re a classic, because caramel and milk chocolate will never go out of style or favour! To be honest, I’m surprised that I like them as much as I do because I’m not a fan of Hershey’s chocolate at all. I’m a diehard Cadbury fan! Fun fact – Hershey’s only manufactures Rolo for the US. Nestle manufactures them here in Canada. Still, it’s not Cadbury!

I first made these cookies last fall. In fact, the pictures you see in the photographs were taken on November 25, 2020. Every year I make lots of extra recipes for my 24 Cookies of Christmas series. Sometimes, I have more than I need, so I either photograph them again without any Christmas props. Or, I wait until the following Christmas to share the recipe with you – just like I did in this case. Can you believe I have had this cookie recipe ready to publish for 12 months!? How’s that for being prepared? Ha!

Speaking of 24 Cookies of Christmas…

LORD BYRON’S 24 COOKIES OF CHRISTMAS – VOLUME 4

Can you believe this is my fourth consecutive year of sharing my 24 Cookies of Christmas advent with you? I have to tell you, it wasn’t easy to bring this series back for the fourth year. The first three years consisted of 24 cookie recipes each, for a total of 72 recipes. I had to get really creative this year in hopes of posting 24 more Christmas cookie recipes.

You might be asking yourself, how many Christmas cookie recipes could one possibly have or need? Well, I say you can never have too much of a good thing. And, I love having lots of choices. Who wants to bake the same holiday cookies year after year?

So, welcome, Dear Reader, to Volume 4 or Lord Byron’s 24 Cookies of Christmas! If you’re new to Lord Byron’s Kitchen, it’s really simple. I share a new recipe every single day for 24 consecutive days – yes, even on Saturday and Sunday. Today’s cookie, this delicious and beautiful Rolo Stuffed Cookie, is day ten. We’re almost to the middle of the countdown. How many of the recipes have you tried yet? Or are you waiting to decide until you see all of the cookies in this series? Speaking of which…

INGREDIENTS NEEDED FOR THIS RECIPE

• Butter – Make sure your butter is at room temperature! You can use salted or unsalted butter. If you use salted butter, do not add the additional 1/4 teaspoon of salt further down the ingredient list.
• Egg – One large egg is all you need. Whenever you set out to bake, make sure your eggs are at room temperature too – just like your butter!
• Vanilla Extract – Probably the most common extract and the most common flavouring used in cakes and cookies.
• Sugar – Sugar will caramelize when baked, which will help to brown cookies and cakes.  In cookies, the sugar will help the dough to spread, and will create a crispness to the bottom of the cookie.
• Brown Sugar – First of all, it has way more flavour than regular white sugar! And, in this recipe, brown sugar helps to keep the cookie moist and soft.
•  Flour – No need for anything special. Just use regular all-purpose flour. I have not tried this recipe with any other type of flour.
• Cocoa Powder – Use good quality cocoa powder, not the kind we used to stir into milk as kids!
• Baking Soda – Commonly known as sodium bicarbonate, or just bicarb, it is a baking ingredient that’s activated by a liquid and an acid to help with leavening or rising. 
• Salt – This is a common ingredient in baking and cooking.  In baking it helps to enhance and balance sweetness. 
• Rolo Chocolate Candy
• Sanding Sugar – Coarse sugar, sometimes referred to as sanding sugar, is used sometimes for decorative purposes.  It is sometimes called pearl sugar or coarse baking sugar.

IS SANDING SUGAR AND GRANULATED SUGAR THE SAME THING?

I get so many questions about the different kinds of sugars. Unless you’re a full-time baker, or really in tune with baking ingredients, it can be a little overwhelming. I use sanding sugar quite often and I hope it’s not too difficult for you to find. Sanding sugar is sometimes referred to as baking sugar, and there are some substitutes.

You can use other sugars – which are basically the same, but named something differently – there’s pearl sugar and coarse sugar. You cannot, however, use granulated sugar. Let me explain why.

Whereas an individual granule of sanding sugar is large and hard, a single granule of granulated sugar is quite small. Sanding sugar will hold up to the heat in your oven without melting; granulated sugar will not. These cookies are baked at 375 degrees F. I would only recommend granulated sugar if the temperature was at a maximum of 350 degrees F.

If you can only find granulated sugar, you can either skip the coating in the sugar step, or you can use turbinado sugar. Turbinado sugar is a golden brown though, so it will throw off the colour of your finished cookie. Wilton calls it sparkling sugar.

CANDY OPTIONS

Rolo candy can be found almost anywhere. Every grocery store, gas station, Walmart, etc., will carry them. You can even source them on Amazon right here. If, however, you don’t care for Rolo candy, you can certainly use other types of candy. To be honest, any chocolate candy with a soft caramel center will work in these cookies. Don’t worry too much about the caramel and the chocolate melting in the oven. They are surrounded by cookie dough, so it will lock in all of that chocolate and caramel goodness.

Hershey’s once had a chocolate kiss with a caramel center. You can use that instead, although the pointy candy might affect the overall appearance of your finished, baked cookie. Try using Milk Duds, or even Riesens. You really don’t need to use chocolate with a caramel center all if you don’t want to, but the gooey goodness of this recipe would all be lost on a non-caramel candy.

Whatever you choose to use, keep in mind that the shape of your cookie will partially be determined by the shape of the chocolate. The size will also be affected. For example, a Milk Dud is much smaller than a Rolo. Speak of, you can use mini Rolos and cut back on the amount of cookie dough you’re using for each cookie. This way, you’ll get smaller cookies, but more of them!

HOW TO MAKE THE COOKIE DOUGH

Don’t be intimidated by the fact that you will need to wrap the cookie dough around chocolate. I’m going to walk you through it so that you will have beautiful cookies and all of that chocolaty caramel goodness will be locked inside and not pouring out onto the baking sheet. It’s really quite easy. Start by preheating your oven to 375 degrees F. Line a baking sheet with a silicone liner or parchment paper and set that aside.

In a large mixing bowl, beat together the butter, granulated sugar, and brown sugar until it is light and fluffy. This will take about 3 minutes. Next, add the egg and vanilla extract. Beat those in too until well combined with the butter and sugar mixture. Set that aside and combine the flour, cocoa powder, baking soda, and salt in a bowl. Whisk those together until combined.

Lastly, add the flour mixture to the butter and sugar mixture. With a low speed on the mixer, beat until just combined. It’s important to not overmix the cookie dough, but be sure that all of the flour is absorbed into the wet ingredients. Set the mixer aside and use a rubber spatula to scrape down the sides of the bowl. That’s it – the cookie dough is ready!

ASSEMBLING THE COOKIES

If you are using full-size/regular-size Rolo candy, you will need to use a tablespoon of the cookie dough. If, however, you have decided to use mini Rolo or another alternative that is smaller as well, then use a slightly rounded teaspoon amount of cookie dough. When you roll the cookie dough around the Rolo there’s just one goal. You want to make sure that the cookie dough completely covers the candy so that when the candy melts in the oven, it doesn’t spill out and leak all over your baking sheet. Here’s how I do it.

Before you start, place the sanding sugar into a shallow bowl. You will need to roll the cookies into the sugar, so have the sugar ready to go. Ok, now, measure out the amount of cookie dough you need. Roll it into a ball. Holding the ball in the palm of your hand, use your index finger on your other hand to push a hole into the ball, but do not push all the way through. Nestle a Rolo candy into the hole and fold the cookie dough over it. Roll the ball again to seal the dough around the candy. Finally, roll the ball into the sugar and place it onto a baking sheet that has been lined with parchment paper.

Continue to roll the cookies, placing them about two inches apart onto the baking sheet. Once done, bake the cookies for 10 minutes. (If you are preparing smaller cookies, bake them for 6-7 minutes.) Once done, remove the cookies from the oven and allow them to cool on the pan for 5 minutes before transferring them to a cooling rack to finish cooling. These bake best when baking one tray at a time.

IF YOU HAPPEN TO HAVE THESE COOKIES SITTING AROUND TOO LONG:

If you don’t finish the cookies before they start to turn stale, don’t toss them out! Place the cookies onto a plate and microwave for 20-30 seconds. Loosely crumble the warm cookies over vanilla ice cream and top with caramel or chocolate sauce. The cookies will taste fresh again. Warm cookies and ice cream are bound to be someone’s favourite treat!

STORING, PACKAGING, & FREEZING

When it comes to most cookies, they taste best at room temperature, but they don’t hold up well to being left out on your countertop for long periods of time. Cookies will stay fresh in a cookie jar or food-safe container with a lid for 3-5 days if left to sit on your kitchen countertop. You can store them in a food-safe container in your fridge. When you want one, two, or half a dozen, take them out of the container and place them in a single layer on a plate. Let them sit at room temperature for 5 minutes and they’re ready!

If you plan to freeze your Rolo Stuffed Cookies, you certainly can! Once they are completely cooled, pile them into a clean, food-safe container. The container must be freezer friendly! You’ll want to ensure a very tight-fitting lid too. I use these quite often when freezing baked goods. I like to place a sheet of plastic wrap over the top of the container before pushing the lid on. This helps to create a better seal. The goal is to keep all of that freshness locked in!

You can freeze these cookies for up to three months. If you plan to give previously frozen cookies as a gift, I would lay them out on a wire cooling rack to thaw completely. Once thawed, pile into cellophane bags and tie with a ribbon, or stack in a cookie tin/box.

QUESTIONS?

If I have not answered all of your questions in the text above, don’t hesitate to reach out to me! You can contact me by sending me a message in the comments section further down the page. I will try my best to answer as soon as possible! You might reach me even faster by following me on Facebook and sending me a private message. Scroll down to follow me and never miss another recipe!

Finally, as I stated previously, every day I will be posting a new recipe. If you miss one, don’t fret. You can find my entire collection of Christmas Recipes right here! There are over 100 Christmas recipes and counting. There’s something for everyone! Cheers!