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Chocolate Cinnamon Bear Cookies

Certified 100% Cute and Easy to Make!

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Chocolate Cinnamon Bear Cookies with Chocolate Cinnamon Bear Candies

Do you have a favorite road trip snack? Something that makes the miles fly by? For me, I always get chocolate-covered cinnamon bears; the kind that has just a bit of heat to them so I get my chocolate fix and a little wake-up call in every bite. On my last road trip (Hello ECLIPSE AMERICA!) my bag of bears quickly melted in the hot southern Utah sun, even with the air conditioning on. “There must be a better way”, I thought. Then came the inspiration for Chocolate Cinnamon Bear Cookies!

OXO Good Grips Cookie Press and Non-Stick Pro Cookie Sheet

I recently received some great baking products from OXO, a kitchen tool company that creates exceptional products (I’ve used their stuff for years) to help promote ‘Cookies for Kid’s Cancer.’ It’s a non-profit that helps to bring awareness and raise funds to fight all types of kids’ cancer. OXO has partnered with bloggers around the country to support this cause and help us get baking and fight kids’ cancer!

Chocolate Cinnamon Bear Cookies spread out on a blue and white cloth checkered napkin.

I had TONS of fun using the OXO Good Grips Cookie Press and trying out the 12 different ‘disks’ that came with it (Like flowers, hearts, snowflakes, butterflies, shells, and even a fleur de lis)!  My Chocolate Cinnamon Bear Cookies were a cinch to create and bake, and my kids joined in on the fun too. They loved this new machine that magically created perfect shapes every time!

Chocolate Cinnamon Bear Cookies are a Traditional Shortbread Cookie with a Twist.

The recipe for Chocolate Cinnamon Bear Cookies is a spin on a traditional chocolate shortbread cookie. You can use almost any type of cookie dough in the press if it’s soft, at room temperature, and doesn’t contain any leavening (baking powder, soda, or yeast).

Let’s jump in and I’ll walk you through how I made these cookies!

Creamed butter and sugar in the bowl of a stand mixer for Chocolate Cinnamon Bear Cookies.

Start by creaming butter, sugar, and salt using a stand or handheld mixer. Next, add in eggs and vanilla and mix until smooth and light. Whisk together, flour, cinnamon, cayenne, and dutch processed cocoa powder. Slowly mix in the flour mixture into the butter-sugar mixture until it’s completely mixed in. Your Chocolate Cinnamon Bear Cookie Dough is ready for the cookie press!

Use High-Quality Ingredients for Exceptional Taste.

It’s important to me to use a really high quality/excellent tasting cocoa powder in all my recipes. Dutched processed cocoa is richer, darker, and is preferred in taste testing to traditional cocoa powders. It will make a huge difference in your baking if you can find it. I also added a bit of cayenne pepper when developing this recipe so you can taste the ‘kick’ of the classic cinnamon bear in the cookies!

Adding flour and cocoa to make dough for Chocolate Cinnamon Bear Cookies.

OXO’s fabulous Non-Stick Pro Cookie Sheet made baking these cookies a breeze because it’s loaded with all kinds of features to ensure your cookies bake up perfectly even and never, ever, ever stick!

OXO Non-Stick Cookie Sheet for baking Chocolate Cinnamon Bear Cookies.

It’s time to load the OXO Cookie Press! Just insert the pattern disk of your choice and unscrew the top to load in the cookie dough. What’s great about it is that you can tell that this baby was engineered by cooks~ Its silicone bottom ensures it won’t slip, and it has a nice comfortable handle and ratchet system that is so easy to use.

OXO Cookie Press used to make Chocolate Cinnamon Bear Cookies.
Loading Chocolate Cinnamon Bear Cookies dough into an OXO Cookie Press.
Stainless steel teddy bear pattern disk inserted into the cookie press for Chocolate Cinnamon Bear Cookies.

One press of the handle is all you need to create a perfectly cute cookie! It takes just seconds to fill an entire sheet pan with adorableness!

Using the OXO cookie press to make Chocolate Cinnamon Bear Cookies!

Seriously these are the cutest cookies you will ever make~ I love them!

Chocolate Cinnamon Bear Cookies waiting for their turn in the oven.

I found that baking these little guys to perfection only took me 8 minutes in a 350-degree oven. I’ve seen shortbread recipes that call for higher temps and longer cook times, but these little guys are perfect when they’re just crunchy on the outside but a little soft on the inside. You’re aiming for cookies, not crackers! Let them cool for about 5 minutes before you remove them with a handy dandy OXO Silicone Cookie Spatula. It’s perfectly designed for cookies and even has a rounded edge to help scrape out the dough from a spoon if needed!

Removing Chocolate Cinnamon Bear Cookies with an OXO silicone cookie spatula to cool on a cooling rack.

I sincerely hope you give these Chocolate Cinnamon Bear Cookies a try and that you seriously consider helping out Cookies for Kid’s Cancer. If you like holiday baking at all, you owe it to yourself to try out OXO’s fabulous cookie press!

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Chocolate Cinnamon Bear Cookies

  • Author: Emily
  • Total Time: 18 minutes
  • Yield: Makes about 8 dozen cookies 1x


  • 3 and 1/2 cups all-purpose flour
  • 1/2 cup dutch processed cocoa powder
  • 2 and 1/2 Tablespoons ground cinnamon
  • 1 teaspoon cayenne pepper
  • 3 sticks unsalted butter at room temperature
  • 1 cup granulated sugar
  • 1/2 teaspoon salt
  • 1 tablespoon vanilla extract
  • 2 large eggs at room temperature


  1. Set your oven to heat to 350 degrees.
  2. Whisk together the flour, cocoa powder, cinnamon and cayenne in a mixing bowl and set aside
  3. Cream the butter, sugar and salt together with either a stand or handheld mixer until light and airy. Add eggs and vanilla slowly while mixing and scrape down the sides if needed to fully incorporate.
  4. Slowly add the dry mixture into the butter mixture while mixing until fully incorporated. Spoon dough into a cookie press and press cookies out onto an ungreased baking sheet.
  5. Bake for 8 minutes, rotating once halfway through. Let cookies cool for a couple minutes before removing to a cooling rack. Serve.
  • Prep Time: 10 minutes
  • Cook Time: 8 minutes


  • Serving Size: 2 cookies

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