Preheat oven to convection 350 degrees fahrenheit.

Beat butter until it turns an off white color.

Add in white sugar and brown sugar.

Beat the sugar with the butter until the mixture is fluffy (about 2 minutes).

Add your egg and egg yolk.

Mix in vanilla.

Add flour, baking soda, baking powder, and cinnamon to form your dough.

Make filling by mixing together room temperature butter, cinnamon, and brown sugar.

Make crumble topping by mixing room temperature butter, brown sugar, cinnamon, and flour.

Use a 1/4 cup scoop and flatten out on your hand or tray. Add 1 tbsp of cinnamon filling and fold the edges around it until the filling is safely inside. (Try not to leave pockets for it to seep out).

Put the cookie dough balls on a tray or plate and put in freezer for 10 minutes.

Next, put a single cookie dough ball on your tray. THIS IS YOUR TEST COOKIE. Use this to estimate how many cookies you can fit on your tray and/or how long your cookies need to cook for. (some ovens may have hot spots, where your cooking time may have to differ).

After baking your test cookie, place cookies on your tray, and bake at 350 for 15 minutes.

At the 10 minute mark, pull them out of the oven and sprinkle your crumble topping on your cookies. Then place back into oven for remaining time.

Add powdered sugar and milk into a bowl and mix until it forms an icing texture.

Drizzle icing on top of cookies and your done!

You can store these at room temperature for up to 10 days or in the fridge for 12 days!