Name: Cinnamon Filling Cookies Recipe
Prep time: 25 min
Cook time: 12 min
Total time: 37 min
Cuisine: American
Ingredients: 6 tablespoons salted butter, softened; 3/4 cup brown sugar, packed; 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

Jump to Recipe· 4.6 from 69 reviews

If you’re a cinnamon lover like me, you absolutely have to try this Cinnamon Filling Cookies Recipe. These cookies aren’t just your typical cinnamon treat—they come with a soft, buttery cinnamon filling that oozes out just enough to make every bite dreamy. I’ve made so many cinnamon cookies over the years, but this recipe? It’s hands-down one of my favorites, and I promise you’ll be hooked after just one batch. Stick around, because I’ll walk you through every step to make sure your cookies turn out perfect and full of that warm, sweet cinnamon goodness.

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Why This Recipe Works

Double Layers of Cinnamon: The cinnamon filling inside combined with the cinnamon-sugar coating creates an irresistible cinnamon flavor explosion.
Soft & Chewy Texture: The cream of tartar and careful mixing ensure these cookies stay tender, never tough or dry.
Freeze-Ready Dough: You can prep ahead by freezing shaped dough balls—perfect for last-minute cravings.
Unique Shaping Step: Pushing the cookies back into shape right after baking keeps that gooey filling in and makes them perfectly chewy.

Cinnamon Filling Cookies, cinnamon cookies recipe, soft cinnamon cookies, homemade cinnamon cookies, buttery cinnamon cookies - A close-up view shows a woman's hand picking up one soft cookie from a baking sheet lined with parchment paper. The cookies are light golden brown with swirls of dark chocolate spread unevenly on the top, giving a marbled look. The baking sheet is placed on a white marbled surface. The cookies are round and slightly puffed, with a soft texture visible from the slight cracks and folds on the surface. There are about seven cookies on the sheet, spaced apart evenly. Photo taken with an iphone --ar 2:3 --v 7

Ingredients & Why They Work

Each ingredient in this Cinnamon Filling Cookies Recipe was chosen to balance flavor, texture, and ease. From the rich butter in both the dough and filling to the combination of spices, these cookies come together with simple pantry staples you likely already have. Here’s why each ingredient matters so much.

Cinnamon Filling Cookies, cinnamon cookies recipe, soft cinnamon cookies, homemade cinnamon cookies, buttery cinnamon cookies - Flat lay of a stick of salted butter softened with a smooth creamy texture, a small white ceramic bowl filled with packed brown sugar, a small white ceramic bowl of ground cinnamon, a mound of fine granulated sugar on a simple white ceramic plate, two whole uncracked large brown eggs with clean shells, a small white ceramic bowl of vanilla extract, a heap of spooned and leveled all-purpose flour, a small white ceramic bowl of coarse kosher salt, a small white ceramic bowl of smooth cream of tartar powder, and a small white ceramic bowl of baking soda powder — all ingredients arranged with perfect symmetry on a clean white marble surface, soft natural light, photo taken with an iPhone, professional food photography style, fresh ingredients, white ceramic bowls, no bottles, no duplicates, no utensils, no packaging --ar 2:3 --v 7 --p m7354615311229779997

Salted Butter: Adds richness and moisture; softened butter is key for smooth creaming.
Brown Sugar: Gives the filling that deep caramel-like sweetness and moisture.
Cinnamon: The star spice, providing warmth and that signature flavor in both filling and coating.
Granulated Sugar: Sweetens the dough and helps create a crisp-slightly chewy texture.
Eggs: Bind the ingredients while adding moisture and richness.
Vanilla Extract: Enhances the sweetness and cinnamon flavor with a lovely aromatic note.
All-Purpose Flour: Provides structure while still allowing softness when not overmixed.
Baking Soda: Helps the cookies rise and spread just right.
Kosher Salt: Balances sweetness and enhances all the flavors.
Cream of Tartar: Keeps the cookies soft and chewy by stabilizing the dough.
Cinnamon-Sugar for Rolling: Adds a sweet-spicy crust that complements the gooey filling.

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Note: You’ll find the complete list of ingredients, along with their exact measurements, in the printable recipe card at the bottom of this post.

Tweak to Your Taste

This Cinnamon Filling Cookies Recipe is wonderfully flexible. Over the years, I’ve experimented with little tweaks to match my mood or the season, and you’ll find that you can easily make it your own too.

Less Sugar: I sometimes cut down the sugar in the dough just a bit if I’m not craving it as sweet, but I keep the filling sugary for that special gooey center.
Spice Mix: Try adding a pinch of nutmeg or ground cloves to the cinnamon filling for a holiday vibe I adore.
Gluten-Free Version: I’ve replaced the all-purpose flour with a 1:1 gluten-free blend successfully; just be gentle mixing to keep dough from getting crumbly.
Vegan Adaptation: Use vegan butter and flax eggs, and the dough still comes out great—just keep an eye on baking times as every oven is different.

Step-by-Step: How I Make Cinnamon Filling Cookies Recipe

Step 1: Whip Up the Cinnamon Filling

Start with 6 tablespoons of softened salted butter in a bowl or mixer—beat it until it’s creamy and smooth. This extra step makes your filling luxuriously soft and spreadable. Next, add brown sugar and cinnamon, then beat again until the mixture is silky. Don’t skip freezing the filling balls—forming marble-sized dollops and freezing them for about 20 minutes is the secret to keeping that delicious center intact during baking.

Step 2: Make the Dough (No Mixer Washing Needed!)

Using the same bowl (yes, same one—I love saving dishes), beat the remaining softened butter until smooth. Add granulated sugar and whisk until it’s light and fluffy, scraping often to avoid any sugar lumps. Mix in eggs and vanilla until smooth. Then, carefully incorporate the dry ingredients—flour, baking soda, salt, and cream of tartar—by spooning the dry mixes and mixing only enough to bring them together. Watch out for over mixing; a few flour streaks visible before a final gentle fold is perfect.

Step 3: Fold In the Frozen Cinnamon Filling

Once your cinnamon filling balls are firm, gently fold them into your dough using a spatula or wooden spoon—as tempting as it might be, avoid electric mixers here to keep them intact. This step gives you those cups of cinnamon goo hidden inside each cookie that make this recipe so magical.

Step 4: Shape and Roll

Shape the dough into roughly 2-inch balls—use a cookie scoop slightly overfilled for uniformity. Then roll each ball in a cinnamon-sugar mixture (that combo of 1/3 cup sugar and 1.5 tablespoons cinnamon is my go-to). This outer coating creates a sweet, slightly crackly shell for contrast against the soft interior.

Step 5: Bake & Shape Right After Baking

Bake at 350°F (175°C) for about 11-12 minutes. When you take them out, the cookies might still look shiny and soft, especially where the cinnamon filling oozes out—that’s exactly what you want. Don’t panic if they seem underbaked! Here’s my pro trick: use spoons to gently push the edges back toward the center within the first 60 seconds out of the oven. This step helps keep the filling contained and gives you thicker, chewier cookies. Let them cool on the pan for at least 5 minutes before moving to a wire rack.

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Pro Tips for Making Cinnamon Filling Cookies Recipe

Freeze the Filling Balls: Freezing the cinnamon filling balls is crucial—don’t skip this step if you want that signature melty core to hold up while baking.
Don’t Overmix Dough: Stop mixing when the ingredients are just combined to avoid tough cookies; a few flour streaks before the final fold are fine.
Shape Cookies Immediately: Right out of the oven, reshape your cookies quickly to keep the cinnamon filling from spreading and to retain a thick, chewy bite.
Use Parchment or Silicone Mats: Both work well to prevent sticking and help cookies bake evenly without burning on the bottom.

How to Serve Cinnamon Filling Cookies Recipe

Cinnamon Filling Cookies, cinnamon cookies recipe, soft cinnamon cookies, homemade cinnamon cookies, buttery cinnamon cookies - The image shows a close-up of several small round pastries with a swirled pattern of light beige dough mixed with dark brown cinnamon and sugar filling. Each pastry has a slightly cracked and soft texture, with the dark brown filling concentrated mainly in the center and swirling outward into the lighter dough. The pastries are stacked closely together, filling the entire frame, and the surface they sit on is a white marbled texture. photo taken with an iphone --ar 2:3 --v 7

Garnishes

I like topping these cookies with a very light dusting of powdered sugar once they’re completely cooled; it adds a pretty contrast and a gentle sweetness that pairs wonderfully with the cinnamon. Sometimes, I drizzle a thin glaze made from milk and powdered sugar for a touch of elegance, especially if I’m serving them at a small get-together.

Side Dishes

These cookies are delicious alongside a cold glass of milk (classic for a reason!) but also fantastic with a warm cup of chai tea or black coffee. For brunch, I like to serve them with fresh fruit or a simple cream cheese spread to balance the sweetness.

Creative Ways to Present

For holiday parties, arrange the cookies on a wooden board surrounded by cinnamon sticks and fresh cranberries for a festive touch. I’ve also wrapped small stacks in parchment paper tied with twine to give as gifts, which always goes over well. For a layered dessert, crumble the cookies into yogurt or ice cream to add some cinnamon crunch.

Make Ahead and Storage

Storing Leftovers

I store leftover cookies in an airtight container at room temperature for up to 4 days. I place a slice of bread in the container to help keep them soft—it really works! They might lose some crispness but remain wonderfully chewy thanks to that filling.

Freezing

This dough is freezer-friendly, and I’ve found that shaping and rolling the dough balls first, then freezing them in a ziplock bag is the best method. When I want fresh cookies, I bake them straight from frozen, adding a couple extra minutes to the baking time—no thawing needed. The result remains just as delicious as fresh-baked!

Reheating

To warm up leftover cookies, I pop them in a 300°F oven for 5-7 minutes. This revives the gooey filling and soft texture beautifully without drying them out like a microwave might. Alternatively, a quick 10-15 second zap in the microwave works if you’re in a hurry.

FAQs

Can I use unsalted butter instead of salted butter?

Yes! If you only have unsalted butter, just add an extra 1/4 teaspoon of salt to the dough and filling recipes to balance the flavors. Salt enhances the sweetness and depth, so a little boost ensures the best taste.
Why do I need to freeze the cinnamon filling balls?

Freezing the filling balls helps them firm up, which stops them from melting and spreading too much while baking. This way, each cookie has a lovely gooey center rather than just cinnamon sugar running all over the pan.
How do I prevent these cookies from flattening too much?

The trick is in the shaping step right after baking—quickly pushing the edges back toward the center keeps the cookies thick and chewy. Also, avoid over mixing the dough, which can cause them to spread too much.
Can I make these cookies dairy-free or vegan?

Absolutely! Use vegan butter and substitute eggs with flaxseed eggs or a commercial egg replacer. The texture changes slightly but these cookies still turn out soft and flavorful.
How many cookies does this recipe make?

You’ll get about 33 cookies using this recipe, depending on how large you scoop your dough balls. It’s perfect for sharing or indulging yourself over a week or two.

Final Thoughts

I honestly can’t recommend this Cinnamon Filling Cookies Recipe enough—it’s one of those recipes I turn to when I want a cozy treat that feels special but is actually super easy to make. The way that rich cinnamon filling melts into soft dough is just pure joy. So trust me, get your butter softened, and let’s get baking! I’m excited for you to make these cookies, enjoy them fresh, and maybe turn a few friends into cinnamon-filled cookie fans too.