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In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This should take about 3-5 minutes with an electric mixer or 5-7 minutes by hand.

Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract and milk until just combined.

In a separate medium bowl, whisk together the all-purpose flour, baking soda, and cream of tartar.

Gradually add the dry ingredients to the wet ingredients, mixing with a spatula or on low speed with an electric mixer until a cohesive, soft dough forms. Be careful not to overmix.

Transfer the dough onto a large sheet of plastic wrap. Using a rolling pin, roll the dough into a large, even rectangular shape, approximately 12x16 inches. Place the flattened dough (still on the plastic wrap) onto a baking sheet and chill for 15 minutes to firm up.

While the dough chills, prepare the cinnamon swirl filling. In a small bowl, combine the light brown sugar, ground cinnamon, and melted butter. Mix until a thick paste forms.

After chilling, remove the top layer of plastic wrap from the dough. Spread the cinnamon swirl filling evenly over the entire surface of the flattened dough, leaving a small border around the edges.

Carefully roll up the dough tightly from one long side into a log, using the plastic wrap underneath to assist in the rolling process. Wrap the dough log tightly in fresh plastic wrap and chill for 20 minutes to further firm it up.

Preheat oven to 350°F. Line two baking sheets with parchment paper.

Unwrap the chilled dough log and place it on a clean surface. Using a sharp knife, slice the log into 1/2-inch thick cookie portions. You should get about 12-15 cookies.

Gently press and shape each sliced portion by hand to form a round cookie with a visible cinnamon swirl in the center. Place the cookies 2 inches apart on the prepared baking sheets.

Bake for 10-12 minutes, or until the edges are lightly golden brown and the centers are set. Do not overbake. Let the cookies cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely.

While the cookies cool, prepare the glaze. In a small bowl, whisk together the powdered sugar, milk, and vanilla extract until smooth. If the glaze is too thick, add a tiny bit more milk; if too thin, add a little more powdered sugar.

Once the cookies are completely cooled, brush or drizzle the glaze generously over the top of each cookie.


In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. This should take about 3-5 minutes with an electric mixer or 5-7 minutes by hand.

Beat in the eggs one at a time, mixing well after each addition. Stir in the vanilla extract and milk until just combined.

In a separate medium bowl, whisk together the all-purpose flour, baking soda, and cream of tartar.

Gradually add the dry ingredients to the wet ingredients, mixing with a spatula or on low speed with an electric mixer until a cohesive, soft dough forms. Be careful not to overmix.

Transfer the dough onto a large sheet of plastic wrap. Using a rolling pin, roll the dough into a large, even rectangular shape, approximately 12x16 inches. Place the flattened dough (still on the plastic wrap) onto a baking sheet and chill for 15 minutes to firm up.

While the dough chills, prepare the cinnamon swirl filling. In a small bowl, combine the light brown sugar, ground cinnamon, and melted butter. Mix until a thick paste forms.

After chilling, remove the top layer of plastic wrap from the dough. Spread the cinnamon swirl filling evenly over the entire surface of the flattened dough, leaving a small border around the edges.

Carefully roll up the dough tightly from one long side into a log, using the plastic wrap underneath to assist in the rolling process. Wrap the dough log tightly in fresh plastic wrap and chill for 20 minutes to further firm it up.

Preheat oven to 350°F. Line two baking sheets with parchment paper.

Unwrap the chilled dough log and place it on a clean surface. Using a sharp knife, slice the log into 1/2-inch thick cookie portions. You should get about 12-15 cookies.

Gently press and shape each sliced portion by hand to form a round cookie with a visible cinnamon swirl in the center. Place the cookies 2 inches apart on the prepared baking sheets.

Bake for 10-12 minutes, or until the edges are lightly golden brown and the centers are set. Do not overbake. Let the cookies cool on the baking sheets for 5 minutes before transferring them to a wire rack to cool completely.

While the cookies cool, prepare the glaze. In a small bowl, whisk together the powdered sugar, milk, and vanilla extract until smooth. If the glaze is too thick, add a tiny bit more milk; if too thin, add a little more powdered sugar.

Once the cookies are completely cooled, brush or drizzle the glaze generously over the top of each cookie.
