Preheat the oven to 350°F. Line a 9-inch square baking dish with parchment paper, allowing the paper to hang over two sides.
To a large bowl, add butter and sugar. Using a hand mixer on medium speed, cream together the butter and sugar until light and fluffy.
Add the egg yolks and vanilla. Mix until combined.
In a separate bowl whisk together the flour, cinnamon, and salt.
Slowly add the flour mixture to the butter mixture. Mix on low until combined, scraping down the sides of the bowl as needed.
Working 1 tablespoon at a time, add milk until the mixture is sticky, thick, and well combined.
Press the dough into the bottom of the baking dish. Pierce the dough with a fork in one-inch intervals.
Bake for 35-40 minutes, or until the top is golden brown.
Remove the shortbread from the oven. While the crust is still hot, press it down with a spatula and set it aside to cool while you prepare the chocolate ganache.