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Step 1
Make the pecan pie filling. Combine all ingredients in a small saucepan and cook over medium heat until it just begins to bubble and thicken. This will take about 5 minutes. Immediately take it off the heat and pour it into a clean bowl. Let it cool completely and then refrigerate for about 1 hour until thoroughly chilled.
Step 2
Make the cookie dough. Combine butter, sugar and brown sugar in a large mixing bowl and beat for about 2 minutes until pale and fluffy. Add egg yolk and vanilla and mix well. Mix in milk. Combine flour, baking soda, baking powder and salt in a medium bowl and whisk to blend well. Add the flour mixture to the butter mixture and fold it in until evenly incorporated and the dough is smooth.
Step 3
Cover the bowl and refrigerate the dough for 30 minutes and line 2 large baking sheets with parchment paper.
Step 4
Preheat your oven to 350 degrees F. Line 2 large baking sheets with parchment paper.
Step 5
Scoop 2 tbsp of dough and roll into smooth balls. Press a 1 tsp measure spoon down in the center of each cookie to create a divet. Spoon about 1 teaspoon of filling right into the center and push the sides up or squeeze the cookie towards the center just a bit to contain it. If the cookie dough cracks, just press it together. Place the tray in the fridge for 15 minutes.
Step 6
Bake for 10-12 minutes until the cookie is nicely golden brown all around. Transfer trays to a wire rack to cool for 3 minutes, then transfer cookies individually to the rack to finish cooling.
Step 7
Once cool, sprinkle more chopped pecans on top and drizzle with melted dark chocolate.