Preheat oven to 325°F. Line an 8x8-inch baking dish with parchment paper and set aside.
In a large bowl, beat the butter until light and fluffy.
Add vanilla extract and powdered sugar, mixing until smooth.
Beat in the egg.
Add flour and salt, mixing until a soft dough forms.
In a medium bowl, combine brown sugar, cinnamon, flour, melted butter, and vanilla extract. Stir until fully combined.
Press one half evenly into the prepared pan (lightly oil hands or a measuring cup if sticky).
Spread the brown sugar cinnamon filling evenly over the base layer.
Place remaining dough on top and gently spread to cover (use oiled hands for easier handling).
Bake for 40 minutes, or until the center is set (use a toothpick to check).
Let bars cool in the pan for about 40 minutes.
In a small bowl, mix powdered sugar, cinnamon, and vanilla extract until smooth.
Add 1–2 teaspoons water if needed to reach a spreadable consistency.
Spread icing over completely cooled bars.
Let sit for about 15 minutes until icing sets slightly.
Lift out using parchment paper and cut into bars.