Preheat oven to 350 degrees. Line a baking sheet with parchment paper.

In a mixing bowl, add in the butter, shortening, 1/2 cup dulce de leche caramel and 1 cup granulated sugar. Mix on medium until light and fluffy. It will take about 2 minutes. Scrape down the sides of the bowl.

Add in the egg and vanilla bean paste or extract. Mix on medium until incorporated. Scrape the sides of the bowol

Add in the flour and baking powder and mix until just incorporated.

Using a medium cookie scoop, scoop out the dough. Roll the dough between your two palms.

Add the remaining 1/4 cup of granulated sugar in a small bowl. Roll the balls of dough into the sugar to completely cover them.

Press your thumb into the center of the cookies. Fill the thumb hole of the cookies with the dulce de leche.

Place 6 on the prepared baking tray. Place in the oven and bake for 10 minutes or until the edges are slightly golden.

Remove from the oven and let cool completely.

Add the melting chocolate and shortening in a sandwich bag. Microwave for 30 seconds. Squish it around and microwave for another 30 seconds. Squish it around to make sure everything is completely melted. If not, do another 30 seconds and squish it.

Cut a very small hole in the corner of the sandwich bag. Quickly drizzle the chocolate all over the completely cooled cookies.

Let the chocolate harden and serve.