Name: Cinnamon Cookie Recipe with Filling 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 cup 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· 4.5 from 42 reviews

If you’re craving a cookie that delivers warm, comforting cinnamon flavor wrapped around a soft, chewy texture with a delightful surprise inside, you’re in for a treat! This Cinnamon Cookie Recipe with Filling Recipe is seriously fan-freaking-tastic—it’s got that classic cinnamon roll vibe but in cookie form, and the hidden cinnamon-sugar filling makes it oh-so-memorable. I promise, once you try these, they’ll become a staple in your baking rotation.

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Why This Recipe Works

A Perfect Cinnamon Surprise: The filling inside melts just enough to ooze a little but is contained perfectly by the soft cookie dough.
Soft Yet Structured Dough: The dough’s use of cream of tartar and proper mixing technique keeps cookies tender without falling apart.
Easy Freezing and Make-Ahead: You can prep filling and dough ahead, then bake fresh whenever the craving hits.
Simple Techniques For Big Flavor: Rolling in cinnamon-sugar before baking adds even more delightful spice to every bite.

Cinnamon Cookie with Filling, Cinnamon Cookie Recipe, Soft Cinnamon Cookies, Chewy Cinnamon Cookies, Cinnamon Filled 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

This Cinnamon Cookie Recipe with Filling Recipe uses straightforward pantry ingredients that combine to create a cozy, buttery cookie with a gooey cinnamon center. Each ingredient has a role, so using quality butter and fresh spices really amps things up. Plus, a sprinkle on rolling sugar gives that classic snickerdoodle sparkle.

Cinnamon Cookie with Filling, Cinnamon Cookie Recipe, Soft Cinnamon Cookies, Chewy Cinnamon Cookies, Cinnamon Filled 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 depth; softened butter creams beautifully with sugar for an airy dough.
Brown Sugar: Its molasses notes make the filling extra flavorful and keeps it moist.
Cinnamon: The star spice that provides warmth and that signature cinnamon roll taste.
Granulated Sugar: Sweetens the dough and helps create just the right texture.
Eggs: Bind the dough together and add moisture for softness.
Vanilla Extract: Elevates all the flavors with its sweet, mellow aroma.
All-Purpose Flour: The structure of the cookies; spooned and leveled to avoid dense dough.
Baking Soda & Cream of Tartar: These work together to give a slight rise and tender crumb, much like a snickerdoodle.
Kosher Salt: Balances sweetness and enhances all the other flavors.
Cinnamon-Sugar (for rolling): Adds a sugary spice crust that complements the filling perfectly.

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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.

Make It Your Way

I absolutely love how flexible this Cinnamon Cookie Recipe with Filling Recipe is—you can tweak the filling spice ratio or even try swapping fillings! It’s fun to personalize and make it truly your own.

Variation: One time, I added a pinch of nutmeg to the filling for extra warmth—so good! Feel free to experiment with other ground spices like cardamom or ginger.
Dietary Modification: I’ve successfully made this with dairy-free butter, which works great—just be sure it’s solid enough for the dough texture.
Filling Swap: Try using a caramel or chocolate spread in place of cinnamon filling for a decadent twist.

Step-by-Step: How I Make Cinnamon Cookie Recipe with Filling Recipe

Step 1: Whip Up That Cinnamon Filling

Start by beating softened butter until creamy—this is the magic base that lends richness to the cinnamon-sugar filling. Then mix in brown sugar and cinnamon until silky-smooth. I like using a stand mixer here, but a hand mixer works fine too. Spoon the filling into marble-sized balls, lay them on parchment, and freeze for at least 20 minutes until firm. This step is key for getting those gooey inside pockets without a messy melt-all-over-the-pan situation!

Step 2: Mix the Cookie Dough Like a Pro

Without washing the bowl, cream softened butter and granulated sugar until fluffy—the longer you beat here, the lighter your cookie dough will be. Add eggs and vanilla, beating until smooth and homogenous. In a separate bowl, whisk your flour with baking soda, cream of tartar, and salt, then gently mix it into the wet ingredients. Stop mixing as soon as flour streaks vanish to avoid tough cookies. We’re aiming for tender, not tough!

Step 3: Fold in Frozen Filling Balls Gently

Once your filling balls are frozen solid, fold them into the dough with a spatula—no mixers here! This keeps the balls intact so the cinnamon pockets stay put, nestled inside the dough rather than melting away.

Step 4: Shape, Roll, and Bake to Cinnamon Perfection

Using a large cookie scoop or spoon, form dough balls about 2 inches across and roll them in a cinnamon-sugar mixture for extra spice on the outside. Place on lined baking sheets, spaced generously so they don’t spread into each other too much. After baking at 350°F for 11-12 minutes, the cookies may look a little shiny and soft, but here’s the trick: immediately use spoons to gently push the edges back toward the center to shape them before they crisp. This step thickens and perfects their chewiness, and that oozing cinnamon filling becomes pure bliss.

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Tips from My Kitchen

Freeze Filling Balls First: This makes folding into the dough so much easier and keeps the filling contained.
Don’t Overmix the Dough: I learned this the hard way—overmixing meant tough cookies. Stop as soon as the flour disappears.
Shape Cookies Right After Baking: Use two spoons to push edges inward quickly to prevent filling from leaking and keep those edges chewy.
Use Parchment or Silicone Mats: They make cleanup easy and keep the cookies from sticking despite the cinnamon sugar filling.

How to Serve Cinnamon Cookie Recipe with Filling Recipe

Cinnamon Cookie with Filling, Cinnamon Cookie Recipe, Soft Cinnamon Cookies, Chewy Cinnamon Cookies, Cinnamon Filled 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 usually keep it simple with a light dusting of powdered sugar or a gentle sprinkle of cinnamon on top for that extra cozy touch—I love how it brings a warm vibe without overpowering the gooey filling. You can also drizzle a thin glaze of vanilla icing for a special occasion.

Side Dishes

Pair these with a cold glass of milk or a cup of spiced chai tea for the perfect cozy combo. They’re also killer alongside warm apple cider or coffee if you want to turn them into a full-on treat moment.

Creative Ways to Present

For the holidays, I’ve arranged them on a festive platter lined with cinnamon sticks and fresh pine sprigs. Mini cookie stacks tied with twine make charming edible gifts. Another fun idea is to serve alongside a small bowl of cream cheese frosting for dipping—pure indulgence!

Make Ahead and Storage

Storing Leftovers

I store leftover cookies in an airtight container at room temperature, layered with parchment paper to keep them from sticking. They stay soft and chewy for up to 5 days (if they last that long!). If you prefer them a bit softer, you can add a slice of bread to the container—it helps keep moisture in.

Freezing

I also freeze shaped dough balls rolled in cinnamon sugar in a ziplock bag for up to 3 months. Baking directly from frozen is a breeze—just add 2-3 extra minutes to the baking time and you’re set. This is a lifesaver when guests drop by unexpectedly.

Reheating

To reheat, pop a cookie in the microwave for about 10 seconds or warm briefly in a low oven (300°F) for 5 minutes. This brings back the fresh-baked softness and gently warms that cinnamon filling without drying out the cookie.

FAQs

Can I make this Cinnamon Cookie Recipe with Filling Recipe without a stand mixer?

Absolutely! You can use a hand mixer or even mix by hand with a sturdy wooden spoon, especially for the filling and dough. Just make sure to cream the butter and sugar really well to get that light, fluffy texture which the cookies need for soft chewiness.
What if my cinnamon filling melts too much and leaks during baking?

Freezing the filling balls solid before folding them into the dough is crucial—that keeps them from melting too quickly. Also, shaping the cookies immediately after baking by pushing the edges inward traps the filling and prevents it from spreading too much.
Can I use this recipe to make mini cinnamon cookies?

Sure! Just adjust the size of the filling balls and dough scoops accordingly. Keep in mind baking time will be shorter (around 8-9 minutes), so watch closely to avoid overbaking.
How do I prevent my cookies from flattening too much?

Using cold butter and not overmixing the dough helps maintain structure. Also, spacing the dough balls well on the baking sheet and shaping the cookies right after baking helps keep them thick and chewy.

Final Thoughts

This Cinnamon Cookie Recipe with Filling Recipe always brings a little magic to my kitchen—every bite is like a cozy hug with that hidden cinnamon-rich center. More than just a cookie, it’s a way to bring warmth and smiles to anyone you share it with. I really hope you give it a go; you’ll enjoy the process and the reward just as much as I do. Happy baking, friend!