Soft and Chewy Cinnamon Roll Sugar Cookies: A Comfort Bake for Beginners

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I still remember the first time I tried baking on my own. It was a cold winter afternoon, and I wanted something cozy to fill the kitchen with warmth and aroma. I loved the smell of cinnamon, and sugar cookies always reminded me of childhood holidays. Combining the two seemed like a dream—familiar, yet special. That experiment led to one of the most delightful things I’ve ever made: cinnamon roll sugar cookies.

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If you’re just stepping into the world of baking, these cookies are the perfect start. They’re easy, forgiving, and come together quickly without complicated techniques or specialty tools. What makes this recipe great for beginners is its balance: soft, chewy texture; warm, comforting flavor; and a swirl of cinnamon sugar that gives a nod to classic cinnamon rolls—without the effort of making dough from scratch or waiting for it to rise.

Ingredients and Preparation

You won’t need any exotic ingredients here—just pantry staples and a little patience. Here’s everything you need to make a batch of about 24 cookies.

Cinnamon Sugar Filling

• 4 tablespoons unsalted butter, softened
• ⅓ cup packed brown sugar
• 1½ tablespoons all-purpose flour
• 2½ teaspoons ground cinnamon
• Pinch of salt

Cookie Dough

• 1 cup unsalted butter, softened but cool
• 1⅓ cups granulated sugar
• 1¾ teaspoons pure vanilla extract
• 1 large egg
• 1 large egg yolk
• 2¾ cups all-purpose flour
• ¾ teaspoon baking powder
• 1 teaspoon cornstarch
• ¼ teaspoon salt

Optional Substitutions

• Butter: If you only have salted butter, reduce added salt by half.
• Brown sugar: Dark brown sugar works too; it will give a richer flavor.
• Flour: For a slightly heartier cookie, you can swap out ½ cup of flour for whole wheat flour.
• Cornstarch: While optional, this gives the cookies their tender chew. If unavailable, omit it without replacing.
• Cinnamon: For variety, add a pinch of nutmeg or cardamom to the cinnamon filling.

Step-by-Step Instructions

1. Preheat the Oven

Set your oven to 350°F (175°C). Line two baking sheets with parchment paper. This prevents sticking and helps the cookies bake evenly.

2. Make the Cinnamon Sugar Filling

In a small bowl, combine the softened butter, brown sugar, flour, cinnamon, and a pinch of salt. Mix until fully blended into a soft paste. Place the bowl in the freezer while you prepare the cookie dough. This makes the filling easier to handle later.

3. Prepare the Cookie Dough

Using a hand mixer or stand mixer with a paddle attachment, beat the softened butter and granulated sugar together until light and fluffy—about 2-3 minutes. This step is crucial for texture. Add the vanilla, the whole egg, and the egg yolk. Beat until everything is well combined. Scrape down the sides of the bowl as needed.

In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt. Slowly add the dry mixture to the wet ingredients. Mix just until incorporated; avoid overmixing, which can lead to tough cookies.

4. Layer the Dough with Filling

Take half of the dough and press it gently into the bottom of a clean bowl. Remove the cinnamon filling from the freezer and drop small spoonfuls (about ½ teaspoon at a time) evenly over this layer. Use about half the cinnamon mixture.

Cover this layer with the remaining dough and press down gently. Add the rest of the cinnamon filling on top in the same way.

5. Create Cinnamon Swirls

Using a spatula or clean hands, gently fold the dough a few times to distribute the cinnamon filling. The goal is to swirl, not blend. You want visible pockets and streaks of cinnamon.

6. Shape and Chill

Scoop the dough into 2-tablespoon portions. Each scoop should include both dough and some cinnamon filling. Roll them gently into balls and place them on a plate or small tray. Freeze the dough balls for 10 minutes. This helps the butter firm up and prevents the cookies from spreading too much in the oven.

7. Bake

Place the chilled dough balls onto your prepared baking sheets, spacing them at least 2 inches apart. For thicker cookies, keep them as is. For thinner cookies, gently flatten the tops with your fingers.

Bake for 10-12 minutes, or until the edges are just turning golden and the centers still look slightly underbaked. This ensures a chewy center once cooled.

Allow the cookies to cool on the baking sheet for 5-10 minutes before transferring them to a wire rack.

Beginner Tips and Notes

How to Tell When They’re Done

Cookies can be tricky. If they look fully baked in the oven, they’re probably overbaked. For these cookies, take them out when the edges are firm and lightly golden but the centers still look soft. They’ll firm up as they cool.

What If…

• My dough feels too sticky? Chill it in the fridge for 15 minutes before shaping.
• The cookies spread too much? Make sure the butter wasn’t too warm and don’t skip the pre-bake freeze.
• They look underdone? They’re supposed to. Let them cool completely before judging.
• The cinnamon filling is leaking out? That’s okay—some streaks on the outside add charm and flavor.

Efficiency Hacks

• Soften your butter by cutting it into cubes and letting it sit out for 30 minutes.
• Use a cookie scoop for evenly-sized cookies.
• Double the recipe and freeze half the dough for future use.

Serving Suggestions

These cookies are already packed with flavor, but here are a few ways to serve and enjoy them even more:

• With coffee or tea: Their warm cinnamon flavor makes them perfect for a morning or afternoon break.
• With vanilla or cinnamon ice cream: Sandwich two cookies around a scoop for an easy dessert.
• As a gift: Stack a few in a clear cellophane bag with a ribbon for a cozy homemade present.

Storage Tips

• Store at room temperature in an airtight container for up to 4 days.
• For longer storage, freeze in a zip-top bag with parchment between layers. To enjoy later, let them thaw at room temperature or warm in a low oven for a few minutes.

Engagement Features

If you’re new to baking, this recipe is a gentle entry point. The steps are straightforward, the results are rewarding, and the cinnamon-sugar combination is universally loved. Even if your swirls aren’t perfect or the dough is a bit messy, you’ll still end up with something warm, delicious, and comforting.

Give this recipe a try and see how rewarding baking can be. Have questions or substitutions you want to try? Share your results and ideas. Every baker’s journey is different, and yours starts here—with cinnamon, sugar, and a bit of confidence.