Line your baking sheets with parchment paper and pre-heat your oven to 350°F.
In a large bowl add your softened butter, sugar and vanilla and mix until combined.
Add your salt and flour. Stir until it comes together and the dough forms.
To make the filling, add your brown sugar, cinnamon and softened butter and mix until it’s well combined.
Scoop out a small piece of your shortbread cookie dough and place on your baking sheet lined with parchment paper, slightly flattening it. Add a small spoonful of the cinnamon brown sugar mixture and then top with another small piece of shortbread cookie dough, making sure the edges of the dough connect, forming your poptart cookie.
Continue with the rest of your cookie dough and cinnamon brown sugar mixture.
Bake at 350°F for 8-10 minutes. Remove from oven and let cool.
To make the glaze, add your milk, powdered sugar and cinnamon into a large measuring cup and mix until your glaze forms. If your glaze is too thin, add more powdered sugar or if it’s too thick, add a little bit of milk at a time, until you reach your desired consistency.
Add a small spoonful of your glaze onto each cookie and sprinkle with a dash of cinnamon.
Share and ENJOY!!
