Lu-Ann Simon October 10, 2025

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Cinnamon Roll Cookie Sandwiches

Name: Cinnamon Roll Cookie Sandwiches
Prep time: 1 h
Cook time: 10 min
Total time: 1 h 10 min
Cuisine: American
Ingredients: 1 1/2 cup Brown Sugar; 1/2 cup Powdered Confectioners Sugar; 1 cup Unsalted Butter; 2 Egg; 2 tablespoon Whole Milk; 1 tablespoon Vanilla Extract; 4 cup All-Purpose Flour; 1 1/2 teaspoon Sea Salt; 1/2 teaspoon Baking Soda; 2 teaspoon Ground Cinnamon; 4 ounce Cream Cheese; 1/4 cup Butter; 2 cup Powdered Confectioners Sugar; 1 teaspoon Vanilla Extract

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There’s something special about the aroma of cinnamon wafting through your kitchen, mingling with the sweet notes of sugar and butter, creating an atmosphere that feels both cozy and indulgent. Cinnamon Roll Cookie Sandwiches are not just a treat; they are an experience, perfect for family gatherings or a cozy afternoon with friends. Imagine delighting in these soft, fragrant sandwiches as you sip on a warm cup of coffee or tea, the ultimate indulgence during chilly mornings or festive celebrations.

Reasons to Adore Cinnamon Roll Cookie Sandwiches

Cinnamon Roll Cookie Sandwiches are the perfect blend of chewy cookies and rich frosting, making them a delightful dessert for many occasions. These treats bring together the comforting flavors of cinnamon rolls and the fun of cookie sandwiches, creating a sweet bite that’s hard to resist. Here are just a few appealing reasons why you’ll love making these:

The irresistibly soft texture that melts in your mouth
The familiar, warming flavor of cinnamon
Personalization options for every palate
They can be made ahead and stored easily
Perfect for sharing, gifting, or enjoying alone

Gather These Ingredients

To create your own batch of Cinnamon Roll Cookie Sandwiches, it’s essential to have the right ingredients on hand. Some ingredients provide the base flavor, while others enhance the treat’s overall texture and sweetness. If you’re in need of substitutions, you can use coconut oil instead of butter for a dairy-free option or swap out the cream cheese frosting for a chocolate spread if desired. Here’s what you’ll need:

1 1/2 cup Brown Sugar
1/2 cup Powdered Confectioners Sugar
1 cup Unsalted Butter
2 Egg
2 tablespoon Whole Milk
1 tablespoon Vanilla Extract
4 cup All-Purpose Flour
1 1/2 teaspoon Sea Salt
1/2 teaspoon Baking Soda
2 teaspoon Ground Cinnamon
4 ounce Cream Cheese
1/4 cup Butter
2 cup Powdered Confectioners Sugar
1 teaspoon Vanilla Extract

Step-by-Step Process to Make Cinnamon Roll Cookie Sandwiches

Creating these delectable Cinnamon Roll Cookie Sandwiches is a straightforward and rewarding experience. Follow these steps for delicious results:

Begin by placing the Brown Sugar (1 1/2 cups), Powdered Confectioners Sugar (1/2 cup), and Unsalted Butter (1 cup) into the bowl of a stand mixer fitted with the paddle attachment. Beat at medium speed until the mixture becomes smooth and fluffy, filling your space with a sweet aroma.
Next, add the Egg (2), Whole Milk (2 tablespoons), and Vanilla Extract (1 tablespoon) to the buttery mixture. Continue mixing until everything is well combined, creating a creamy consistency.
In a separate medium bowl, whisk together the All-Purpose Flour (4 cups), Sea Salt (1 1/2 teaspoons), and Baking Soda (1/2 teaspoon) until well combined. This mixture will give structure to your cookies.
Gradually add the flour mixture into the butter mixture, reducing the mixer speed to low. Mix just until combined, avoiding overmixing to keep the cookies tender.
Remove half of the dough from the mixer and set it aside. To the remaining dough, add the Ground Cinnamon (2 teaspoons), mixing until it is fully incorporated. The delightful scent of cinnamon should be blooming at this point.
Shape both portions of dough into balls and then pat them into rough rectangles. Cover each portion and refrigerate for about 1 hour, allowing the flavors to meld together.
Once chilled, preheat your oven to 400 degrees F (205 degrees C).
Roll out each dough into a 9×12-inch rectangle on a lightly floured surface.
Place the cinnamon-flavored dough on top of the plain dough and roll them out together into a 10×14-inch rectangle, blending the flavors beautifully.
Tightly roll the dough from one long edge to the other, then gently roll it back and forth to secure the layers together.
Cut out the cookies, aiming for about 48 pieces.
Arrange the cookies at least 2 inches apart on a prepared baking sheet. Bake in the oven for approximately 10 minutes, until they turn a lovely golden color.
For the frosting, use a stand mixer to cream together the Cream Cheese (4 ounces) and Butter (1/4 cup) until smooth. Gradually add in the Powdered Confectioners Sugar (2 cups) and Vanilla Extract (1 teaspoon), whipping until a velvety frosting forms.
Transfer the frosting into a large zip-lock bag and carefully snip off one of the corners.
To assemble, squeeze about a tablespoon of frosting onto the bottom of one cookie. Top with another cookie to form a sandwich. Continue this process until all cookies are frosted and sandwiched.

Prep ~ 1 hour, Cook ~ 10 minutes, Total ~ 1 hour 10 minutes, Servings ~ 24 sandwiches, Kcal ~ 230 (approx.)

Plan Ahead

If you’re looking to save time, you can prepare the cookie dough ahead of time. Simply follow the steps up to the chilling process, then wrap the formed dough in plastic and store it in the refrigerator for up to three days or in the freezer for up to three months. When you’re ready to bake, just thaw in the fridge overnight and proceed with rolling and cutting.

How to Store Leftovers

To keep your Cinnamon Roll Cookie Sandwiches fresh, store any leftovers in an airtight container in the refrigerator for up to one week. If you want to save them longer, consider freezing them in a single layer, then transferring them to a freezer-safe bag. Thaw at room temperature before enjoying again. For best results, avoid reheating, as they are best enjoyed chilled or at room temperature.

Ideal Pairings

These delightful Cinnamon Roll Cookie Sandwiches can be enjoyed alongside a variety of beverages and snacks, enhancing their flavors beautifully. Consider pairing with:

A steaming cup of freshly brewed coffee, complementing the sweetness while balancing the flavors
Herbal tea, adding a soothing touch, perfect for cozy gatherings
Glasses of cold milk, a classic that never fails to satisfy
Ice cream, to create a sandwich affair that’s exceptionally luxurious
Fresh fruit, adding a refreshing contrast to the sweetness

Make It Your Own

Cinnamon Roll Cookie Sandwiches are versatile and can easily be adapted to suit your tastes. Here are some exciting ideas to customize your creation:

Add chocolate chips to the dough for an indulgent twist
Incorporate chopped nuts for added crunch and flavor
Swap ground ginger for cinnamon for a spiced variation
Drizzle caramel sauce on the frosting for a sweet extra layer
Use food colorings to create festive-themed sandwiches for holidays
Experiment with different extracts like almond or maple for a unique flavor profile
Try adding sprinkles for a fun, colorful finish

Cook’s Notes and Secrets

To ensure your Cinnamon Roll Cookie Sandwiches turn out perfectly every time, consider these helpful tips:

Make sure your butter is softened but not melted for the best texture
Be careful not to overmix the dough as this can lead to tough cookies
Chilling the dough is vital for easy handling and shaping
Keep ample space between cookies on the baking sheet to allow for spreading
Allow cookies to cool completely before frosting to ensure it doesn’t melt

Your Questions, Answered

How can I make these cookies gluten-free?
You can replace the all-purpose flour with a gluten-free flour blend designed for baking.
Can I add flavors to the frosting?
Absolutely! Feel free to mix in additional extracts like lemon or almond for a unique frosting flavor.
What if I don’t have a stand mixer?
You can use an electric hand mixer or mix by hand using a sturdy spatula. It may take a bit more effort, but the cookies will still turn out delicious.
Can these cookies be decorated for holidays?
Yes! Add festive sprinkles or colored frosting to make them suitable for any celebration.
What’s the best way to serve them?
They are best enjoyed at room temperature, paired with your favorite beverage for a comforting treat.

Final Thoughts

Cinnamon Roll Cookie Sandwiches are a delightful fusion of flavors and textures that can warm any gathering. They’re wonderfully easy to make and sure to please just about anyone with a sweet tooth. So gather your ingredients, follow the simple steps, and soon you’ll be creating these irresistible treats that are bound to become a cherished favorite in your household. Make them soon and invite others to enjoy the warmth and sweetness they offer!

Cinnamon Roll Cookie Sandwiches

Author: lu-ann
Total Time: 70 minutes
Yield: 24 servings 1x
Diet: Vegetarian

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Description

Delightful sandwich cookies with the comforting flavors of cinnamon rolls and rich frosting, perfect for any occasion.

Instructions

Beat Brown Sugar, Powdered Sugar, and Unsalted Butter in a stand mixer until smooth and fluffy.
Add Eggs, Whole Milk, and Vanilla Extract; mix until combined.
In a separate bowl, whisk together Flour, Sea Salt, and Baking Soda.
Gradually add flour mixture to the butter mixture on low speed until combined.
Separate half the dough and mix Ground Cinnamon into the remaining half.
Shape both portions of dough into balls, flatten, cover, and refrigerate for 1 hour.
Preheat oven to 400°F (205°C).
Roll out each dough into a 9×12 inch rectangle.
Layer cinnamon dough on top of plain dough and roll into a 10×14 inch rectangle.
Tightly roll the dough from one long edge to the other and cut out cookies (about 48 pieces).
Arrange cookies on a baking sheet and bake for about 10 minutes until golden.
For frosting, cream together Cream Cheese and Butter, then add Powdered Sugar and Vanilla.
Assemble sandwiches by frosting one cookie and topping with another.