Cinnamon Bun Hamantaschen

Cinnamon buns are one of our favourite morning pastries, and we couldn’t resist turning them into hamantaschen! 

The rich butter dough is flecked with cinnamon, which not only tastes good but is so pretty. They’re filled with a brown sugar & cinnamon filling, and are drizzled with a vanilla glaze after baking. They taste just like cinnamon buns, but take half the time to make.

These hamantaschen are the perfect afternoon snack along with a cup of tea, but we’re not judging if you have them for breakfast!


2 ¼ cups all-purpose flour, plus more for work surface
¾ teaspoons baking powder
½ teaspoon ground cinnamon
½  heaping teaspoon kosher salt
½ cup unsalted butter, room temperature
½ cup granulated sugar
1 large egg
1 ½ tsp vanilla extract
1 ½ tbsp milk (dairy or non-dairy)

1 egg, lightly beaten (this egg will be used to brush the hamantaschen rounds before shaping them)

Cinnamon Filling
⅔ cup light brown sugar
1 ½ tbsp ground cinnamon
¼ cup butter, melted

Vanilla Glaze
⅔ heaping cup powdered sugar
1 ¾ tablespoons heavy cream or milk
½ teaspoon vanilla extract or vanilla bean paste


In a small bowl, whisk together the flour, baking powder, cinnamon, and salt. 

In a medium bowl, beat the butter and sugar together until pale and fluffy, about 4 minutes. Add in the egg, mixing until it’s combined. Using a wooden spoon or mixing spatula, mix in the vanilla and milk, until you have a smooth mixture.

Gradually add the dry ingredients into the butter mixture until it’s well incorporated and you have a smooth dough.  If the dough isn’t coming together and seems dry, add in a teaspoon of milk, until you have a dough that’s smooth and holds together. Wrap the dough in plastic wrap and chill for at least 1 hour or up to 24 hours.

While the dough is chilling, make the cinnamon filling. In a small bowl, mix the brown sugar and cinnamon filling together, until they’re combined. Add in the melted butter, and stir to combine. Refrigerate for 10 minutes until firm.

Make the vanilla glaze, in a small bowl mix the powdered sugar, heavy cream or milk and vanilla extract together until smooth. The consistency of the glaze should be pourable, if it is too thick, add heavy cream or milk, a teaspoon at a time until you have a pourable glaze.

Let the disk of dough sit at room temperature for about 15 – 20 minutes, until it’s slightly softened. This is important because if the dough is too cold, it will crack when you try to roll it out.

Preheat the oven to 350 degrees. Line two baking sheets with parchment paper.

Cut the disk of dough in half. Working with one half at a time, lightly dust your work surface with flour to keep the dough from sticking, and roll it out until it’s about ¼ inch thick. Using a 3.5 inch round cookie cutter or glass, cut dough, and, using an offset spatula, place rounds on the prepared baking sheets. Gather the scraps of dough, reroll, and cut out more rounds. 

Working three at a time, brush the edges of the rounds with the beaten egg, and place one slightly heaping teaspoon of the cinnamon filling into the center of each round. Fold the rounds into triangles, pinching the corners to seal, leaving some of the filling exposed in the center of the cookie. 

Once one baking tray is filled with hamantaschen and place the tray in the freezer for 10-15 minutes. This will prevent the hamantaschen from splitting open as they’re baking. 

Repeat with remaining dough.

Bake for 12-15 minutes until the bottoms of the cookies are golden brown. Remove from the oven, and let cool on baking sheets. Once the hamantaschen are completely cool, drizzle with vanilla glaze.


Store the hamantaschen in an airtight container at room temperature for up to 5 days.

16 – 18 hamantaschen
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