These Cinnamon Roll Sugar Cookies combine two classic favorites into one irresistible treat. Imagine soft, buttery sugar cookies swirled with a rich cinnamon-sugar filling just like a freshly baked cinnamon roll. The result is tender cookies packed with warm spice, sweet flavor, and beautiful cinnamon ribbons throughout — perfect for holidays, cozy afternoons, or anytime you want a comforting homemade dessert.
4 tablespoons unsalted butter, softened
⅓ cup brown sugar, packed
1½ tablespoons all-purpose flour
2½ teaspoons ground cinnamon
Pinch of salt
1 cup unsalted butter, softened but cool
1⅓ cups granulated sugar
1¾ teaspoons vanilla extract
1 large egg
1 large egg yolk
2¾ cups all-purpose flour
¾ teaspoon baking powder
1 teaspoon cornstarch
¼ teaspoon salt
Preheat oven to 350°F (175°C) and line two baking sheets with parchment paper.
In a small bowl, mix butter, brown sugar, flour, cinnamon, and salt.
Stir until fully combined into a thick paste.
Freeze for 10 minutes to firm up while preparing the dough.
Beat butter and granulated sugar until light and creamy.
Add vanilla extract, egg, and egg yolk. Mix until smooth.
In another bowl, whisk flour, baking powder, cornstarch, and salt.
Gradually add dry ingredients to wet ingredients and mix until just combined.
Remove half of the dough and set aside.
Spread remaining dough in the mixing bowl.
Scatter small pieces of chilled cinnamon filling over dough.
Add reserved dough on top and gently press.
Sprinkle remaining cinnamon filling over the top.
Fold dough gently only 1–2 times to create swirls without blending completely.
Scoop 2-tablespoon-sized dough balls.
Ensure each contains cinnamon filling pieces.
Freeze dough balls for 10 minutes to prevent spreading.
Place dough balls a few inches apart on baking sheets.
Keep dough mounded for thick cookies or flatten slightly for thinner ones.
Bake for 10–12 minutes, until edges are lightly golden and centers look slightly soft.
Allow cookies to cool on baking sheets before transferring to a wire rack.
They will firm up while cooling while staying soft inside.
✅ Spoon and level flour to avoid dense cookies.
✅ Do not overmix after adding cinnamon filling.
✅ Chill dough balls for thicker cookies.
✅ Reshape warm cookies gently for perfect rounds.