In a large mixing bowl, cream together ½ cup softened unsalted butter and 1 cup granulated sugar until the mixture is light and fluffy, about 3–4 minutes. Add 2 large eggs and 1 teaspoon of pure vanilla extract, mixing thoroughly. Gradually incorporate 2 cups all-purpose flour, 1 teaspoon baking powder, ½ teaspoon baking soda, and a pinch of salt until a cohesive dough forms.

Once your cookie dough is well-formed, cover the bowl with plastic wrap and place it in the refrigerator for about 30 minutes.

While the dough chills, prepare the cream filling. In a medium bowl, whisk 1 cup of heavy cream until soft peaks begin to form. Gradually blend in ½ cup powdered sugar and 1 teaspoon vanilla extract until the mixture is smooth and fluffy.

Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper. Scoop tablespoon-sized portions of the chilled dough onto the prepared sheet, spacing them about 2 inches apart. Bake in the preheated oven for 12–15 minutes or until the edges are lightly golden.

While the cookies cool, make the chocolate glaze. In a microwave-safe bowl, combine 1 cup semi-sweet chocolate chips with 1 tablespoon vegetable oil. Heat in the microwave in 30-second increments, stirring each time, until smooth and glossy.

Once the cookies are completely cool, fill the center of half of the cookies with the chilled cream filling, then drizzle the warm chocolate glaze generously over the tops.