Heat oven to 350 F. Line a 9×9-inch square baking pan with parchment paper, leaving some excess paper hanging over the sides of the pan.

To make the shortbread crust: In the bowl of a stand mixer fitted with the paddle attachment, combine the butter, sugar and salt. Beat on medium speed until light and fluffy, 5 minutes. Reduce the speed to low and mix in the egg yolk and vanilla until incorporated, 1 minute. Scrape down the sides of the bowl and add the flour. Continue mixing until a dough forms, 1 minute.

Transfer the dough to the prepared baking pan and press down into an even layer. Bake for 20 to 25 minutes until set and golden brown on the edges. Let cool for 15 minutes.

To make the dulce de leche: In a medium saucepan, combine the sweetened condensed milk, butter, brown sugar, corn syrup, salt and cinnamon. Cook over medium heat, stirring constantly, until the dulce de leche bubbles and registers 225 F on an instant-read thermometer, about 12 minutes. Immediately pour the dulce de leche caramel over the cookie layer and spread to the edges of the pan. Transfer to the refrigerator and allow to cool at least 15 minutes or up to overnight.

To make the ganache: In a heatproof bowl, combine the bittersweet chocolate, cream, ancho powder and chipotle powder. Fill a small pot ¼ full with water. Bring to a simmer. Set the bowl on top of the pot, making sure the bottom of the bowl is not touching the water. Stir constantly over low heat until the chocolate is melted and the mixture is smooth, about 6 minutes.

Pour the ganache over the caramel layer, spread into an even layer and return the pan to the refrigerator. Allow to set for at least 1 hour or up to overnight before serving.

Remove from the pan and cut into 16 square bars. Serve cold.