Name: Cinnamon Cookie Sandwiches with Rich Cinnamon Filling Recipe
Prep time: 15 min
Cook time: 12 min
Total time: 36 min
Cuisine: American
Ingredients: 6 tablespoons salted butter, softened; 3/4 cup packed brown sugar; 1 and 1/2 tablespoons cinnamon; 1 cup salted butter (2 sticks), softened; 1 and 2/3 cups granulated sugar; 2 large eggs; 2 teaspoons vanilla extract; 3 and 1/2 cups all-purpose flour, spooned and leveled; 1 teaspoon baking soda; 3/4 teaspoon kosher salt; 1 and 1/2 teaspoons cream of tartar; 1/3 cup granulated sugar; 1 and 1/2 tablespoons cinnamon

I absolutely adore these Cinnamon Cookie Sandwiches with Rich Cinnamon Filling Recipe because they combine everything I love about cinnamon in one delightful bite—soft, chewy cookies carrying a luscious, creamy cinnamon filling that melts in your mouth. From the first taste, I knew this was a recipe I wanted to share with everyone who craves that warm, spicy sweetness paired with buttery richness, perfect for both everyday treats and special moments.

Why You'll Love This Cinnamon Cookie Sandwiches with Rich Cinnamon Filling Recipe

What makes this recipe stand out so much for me is the incredible balance of flavors. The cookies themselves are wonderfully tender with a subtle crisp on the edges, but the star is absolutely the rich cinnamon filling hidden inside. It delivers that glorious, deep cinnamon flavor packed with just the right amount of sweetness and a hint of molasses from the brown sugar. Every bite tastes like a cozy cinnamon roll in cookie form!

I also love how straightforward this recipe is to make, even if it looks fancy once finished. The ingredients are simple pantry staples, and the process feels fun—especially when you get to freeze those cinnamon filling balls and then fold them into the dough. It feels like a little homemade magic is happening in the kitchen. I often find myself baking these for holiday parties, weekend gatherings, or whenever I want to impress friends with a comforting, irresistible treat.

Another reason I'm so excited to share this Cinnamon Cookie Sandwiches with Rich Cinnamon Filling Recipe is that it elevates a classic cookie into a special dessert without adding complexity. It’s perfect for family dinners as a sweet ending, a festive afternoon snack, or even a charming gift wrapped up for neighbors. Trust me, once you try them, they will become one of your beloved go-to cookie recipes just like they are for me.

Ingredients You'll Need

The image shows close-up of round cookies with swirls of light golden brown and dark brown cinnamon sugar on the top layer. The cookies have a soft, slightly crumbly texture with some sugar crystals visible on the surface. One cookie in the center has a bite taken out, showing a pale yellow inside. The cookies lie on a parchment-lined surface with a few crumbs scattered around. The overall colors are warm shades of beige, tan, and brown. photo taken with an iphone --ar 4:5 --v 7

The beauty of this recipe lies in its combination of simple but essential ingredients, each bringing something unique to the table—whether that’s flavor, texture, or richness. Every single item plays a vital role in creating those soft, chewy cookies and the creamy, spiced filling that sets this treat apart.

TIP : You'll find the full list of ingredients and measurements in the recipe card below

Salted butter: Provides the rich, creamy base for both dough and filling, adding moisture and flavor.
Brown sugar: Gives the filling its deep molasses sweetness and moist texture.
Cinnamon: The star spice that delivers warmth and that unforgettable cinnamon aroma.
Granulated sugar: Sweetens the dough and helps achieve a light, fluffy texture after creaming.
Large eggs: Bind everything together while adding moisture and richness.
Vanilla extract: Enhances all the flavors with a subtle sweetness and depth.
All-purpose flour: The structure of the cookies, spooned and leveled for the perfect texture.
Baking soda: Helps the cookies rise just right for that tender crumb.
Kosher salt: Balances sweetness and elevates all flavors in the dough.
Cream of tartar: Adds chewiness and helps with the cookie’s texture and appearance.
Cinnamon sugar blend: For rolling the dough, adding a classic sweet-spice crust outside the cookie.

Directions

Step 1: Start by making the cinnamon filling. Beat 6 tablespoons of softened butter in a large bowl or stand mixer until creamy and smooth. Add ¾ cup packed brown sugar and 1 and ½ tablespoons cinnamon, then beat until fully combined and smooth.

Step 2: Line a baking sheet with parchment paper or a silicone mat, then use a spoon to form the filling into small marble-sized balls. Place them on the prepared sheet and pop them into the freezer for about 20 minutes until firm. If your freezer is full, refrigerate instead but expect longer chilling time.

Step 3: Preheat your oven to 350°F (175°C) and prepare two baking sheets with parchment or silicone mats for the cookies.

Step 4: In the same mixing bowl (no washing needed), beat 1 cup of softened butter until smooth and creamy. Gradually add 1 and ⅔ cups granulated sugar and beat on medium-high until light and fluffy, scraping the bowl sides regularly.

Step 5: Add two large eggs and 2 teaspoons of vanilla extract to the butter mixture, beating until smooth and homogeneous.

Step 6: Spoon and level 3 and ½ cups of all-purpose flour into a separate bowl. Stir in 1 teaspoon baking soda, ¾ teaspoon kosher salt, and 1 and ½ teaspoons cream of tartar, then slowly mix this dry blend into the wet ingredients. Mix just until combined; a few flour streaks are okay.

Step 7: Use a spatula to fold the mixture until there are no more dry streaks, making sure not to overmix, or the cookies will become tough.

Step 8: Retrieve your frozen cinnamon filling balls and gently fold them into the cookie dough using a spatula or wooden spoon—avoid mixers to keep the filling balls intact.

Step 9: Scoop dough into large balls roughly 2 inches across, then roll each ball in a mix of ⅓ cup granulated sugar combined with 1 and ½ tablespoons cinnamon, coating them well.

Step 10: Place the cookies on prepared baking sheets, leaving at least 2 inches between each to allow for spreading. I usually put 8 to 12 cookies per sheet, depending on space.

Step 11: Bake at 350°F for 11 to 12 minutes. The edges of the cookies should be firm but not golden, and the filling will appear shiny and slightly spread out.

Step 12: As soon as the cookies come out of the oven, work quickly! Use two spoons to push the edges toward the center and gently pack the filling back in if it has ooze out. This gives the cookies their perfect thick, chewy texture.

Step 13: Let the cookies cool on the pan for at least 5 minutes, then transfer to a wire rack to cool completely or enjoy warm with a cold glass of milk or your favorite beverage.

Step 14: (Optional) Freeze any remaining dough balls after rolling in cinnamon sugar in a zipped bag for up to three months. Bake from frozen, adding a few extra minutes to the baking time.

Servings and Timing

This recipe makes about 33 delicious cinnamon cookie sandwiches, perfect for sharing or enjoying over several days. The preparation takes about 15 minutes for the filling and dough, plus chilling and freezing time for the filling balls. Baking is quick at around 11-12 minutes per batch, though you should allow a total of approximately 36 minutes active cooking and baking time. Don’t forget the crucial resting period for the cookies on the pan and to freeze the filling balls ahead for best results.

How to Serve This Cinnamon Cookie Sandwiches with Rich Cinnamon Filling Recipe

A close-up view of a stack of cinnamon roll cookies showing four visible layers with a soft, crumbly texture. Each layer shows a mix of golden-brown dough and dark cinnamon-sugar swirls creating a marbled effect throughout. The outer part is lightly golden with a dusting of cinnamon sugar, and one cookie has a bite taken out, revealing the soft inside. The cookies sit on a white marbled surface with a few cinnamon crumbs scattered around. Photo taken with an iphone --ar 4:5 --v 7

When I serve these cookies, I like to treat them like the star attraction of a cozy dessert spread. They pair beautifully with a cold glass of milk if you want to keep it classic, especially for kids or casual treats. But for adult gatherings, I love offering a lightly spiced chai tea or a robust coffee with a touch of cream. The warm spices in those drinks complement the cinnamon perfectly.

Presentation-wise, I like to arrange the cookies on a simple wooden board or white platter sprinkled lightly with extra cinnamon sugar to echo the flavors inside. Garnishing with a small dusting of powdered sugar can add a pretty snowy effect, especially in the winter months. For parties or festive occasions, adding a side bowl of whipped cream or a cinnamon-spiced dipping sauce can make the experience even more decadent.

These cookies are just perfect served slightly warm to enjoy that gooey cinnamon filling at its best. If you chill them, I recommend letting them come to room temperature before eating so the filling softens up nicely. They are delightful for holiday cookie exchanges, afternoon snacks, or even as a thoughtful homemade gift nestled in a pretty tin.

Variations

Over time, I’ve found some fun ways to switch things up with this Cinnamon Cookie Sandwiches with Rich Cinnamon Filling Recipe. For example, swapping out all-purpose flour for a gluten-free blend makes these cookies accessible to friends with gluten sensitivities, and they turn out just as delicious and chewy. If you prefer vegan options, replacing the butter with plant-based alternatives and using flax eggs can work well, although the texture may be a touch different but still satisfying.

You can experiment with flavor variations too—adding a pinch of nutmeg or ground cloves to the cinnamon filling introduces warm undertones that take the spice profile to the next level. Or for a chocolate twist, mix mini chocolate chips into the dough or roll the baked cookies edges in finely chopped nuts or cocoa powder for extra dimension.

For a different technique, I sometimes like to chill the dough overnight without adding the frozen cinnamon balls and then sandwich the filling between two smaller cookies once baked for a handheld treat reminiscent of classic sandwich cookies but bursting with cinnamon goodness.

Storage and Reheating

Storing Leftovers

After baking, I store leftover cookies in an airtight container at room temperature for up to 4 days. Using a container with a tight seal keeps them soft and chewy, preserving that delightful cinnamon filling inside. I prefer layering the cookies between parchment paper to prevent sticking, especially if they’re still slightly warm when stored.

Freezing

If you want to freeze finished cookies, wrap them individually in plastic wrap and store them in an airtight freezer bag or container. They’ll keep well for up to 2 months. When frozen right after baking and cooling, you can thaw them overnight at room temperature or warm gently in the oven. I also freeze raw dough balls rolled in cinnamon sugar for up to 3 months, baking them fresh from frozen as needed.

Reheating

To bring back the soft, melty magic of these cookies, I like to warm them in a 300°F oven for 5-7 minutes. Avoid microwaving if possible, as it can make the cookies rubbery or dry out the edges. Warming just enough restores that luscious, gooey cinnamon filling without losing the tender chew I love so much.

FAQs

Can I use unsalted butter instead of salted butter?

Absolutely! If you use unsalted butter, just add a pinch more salt to the dough to make sure the flavors stay balanced. Salted butter adds a subtle depth and seasoning that enhances the cinnamon and sweetness, so don’t skip the salt entirely.

What if I don’t have cream of tartar?

Cream of tartar helps keep these cookies chewy and affects their texture, but if you don’t have it, you can substitute with an equal amount of baking powder since it contains cream of tartar and baking soda. However, your cookies might spread a bit more and be slightly less chewy.

Can I make the cinnamon filling balls ahead of time?

Yes! In fact, freezing the cinnamon filling balls before mixing them into the dough is key for this recipe. It prevents the filling from melting too quickly in the oven and helps maintain the cookie’s shape and thick texture. I often prepare the filling balls a day before baking.

How do I prevent the cinnamon filling from leaking too much?

Right after baking, the filling can be gooey and runny, but shaping the cookies quickly with two spoons within the first minute out of the oven pushes the filling back into the dough and thickens the cookie overall. This step is essential to prevent spreading and keep that thick sandwich-style texture.

Can I double this recipe for larger batches?

Definitely! This recipe scales up well, but make sure you have enough freezer space for the filling balls and multiple baking sheets to keep up with the baking process. Adjust baking time slightly if your cookies are larger or your oven is crowded.

Conclusion

I truly hope you give this Cinnamon Cookie Sandwiches with Rich Cinnamon Filling Recipe a try because it’s become one of my absolute favorite cookies to bake and share. The combination of soft, tender dough and that rich cinnamon filling is utterly unforgettable, and I guarantee it will warm your heart and your kitchen. Whether you’re baking for loved ones or treating yourself, these cookies bring a perfect touch of comfort and joy to any day.