In a medium bowl, whisk together 2 cups of all-purpose flour, ¾ cup of cocoa powder, 1 teaspoon of baking powder, ½ teaspoon of baking soda, and ½ teaspoon of salt until well combined. Set aside.

In a stand mixer, cream together ½ cup of unsalted butter, ½ cup of light brown sugar, and ½ cup of granulated sugar until light and fluffy, about 3-4 minutes. Add eggs one at a time, then mix in vanilla extract and vegetable oil. Gradually add dry mixture, mixing until just combined.

Transfer dough to plastic wrap, shape into a disc, wrap tightly, and refrigerate for at least 5 hours.

Preheat oven to 180°C (350°F) and line baking sheets with parchment paper.

Scoop tablespoon-sized dough, roll in turbinado sugar, and freeze for about 15 minutes.

Bake cookies for 7-8 minutes until slightly underbaked in the centers. Cool on baking sheet for 5 minutes before transferring to a wire rack.

In a saucepan, heat 1 cup of granulated sugar until melted into a rich, amber-colored liquid, then add 6 tablespoons of unsalted butter and whisk until combined. Gradually pour in ½ cup of heavy cream and whisk until smooth.

Spread about 1 teaspoon of caramel filling on one cookie half, press another half on top, and repeat until all cookies are filled.