In a large bowl add the granulated sugar, 1/2 cup brown sugar and the softened butter. Use an electric mixer to beat on high speed until mixture is creamy.
Add in the egg, 1 teaspoon vanilla extract and bourbon to the bowl and beat until mixture is well incorporated.
In a separate medium bowl whisk together the flour, baking powder, salt and cocoa powder until combined.
Slowly add in the flour mixture into the wet ingredients in 2-3 intervals, beating after each interval, until the flour mixture is well mixed. Cover the dough and refrigerate for at least 30 minutes until it is firm.
Once dough is chilled preheat your oven to 350 degrees F. Line 2 cookie sheets with parchment paper.
Shape dough into 1 1/4 inch balls. Place at least 2 inches apart on the prepared cookie sheets. Flatten each ball slightly, then use your thumb to make an indentation in each cookie.
In a medium bowl combine the pecans, remaining 1/2 cup brown sugar, 1 teaspoon vanilla extract, and heavy cream and mix until combined. Fill the indentation in each cookie with about 1 teaspoon of filling.
Bake in the preheated oven for 10-12 minutes, until they appear set. Cool for 5 minutes, then remove to a cooling rack to cool completely.
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