01 - Preheat oven to 350°F. Line a baking sheet with parchment paper.
02 - In a bowl, whisk together flour, baking powder, baking soda, and salt until well blended.
03 - In a separate bowl, beat softened butter and granulated sugar until light and fluffy, approximately 2-3 minutes. Add egg and vanilla extract, mixing until incorporated.
04 - Gradually add dry ingredients to the butter mixture, alternating with milk. Mix until a soft dough forms, being careful not to overmix.
05 - Scoop tablespoon-sized portions of dough and roll into balls. Arrange on prepared baking sheet with 2 inches of space between each. Flatten slightly with palm.
06 - Bake for 10-12 minutes until edges are lightly golden. Transfer to wire rack and cool completely before filling.
07 - Combine milk, sugar, egg yolk, cornstarch, vanilla, and salt in a saucepan. Cook over medium heat, whisking continuously, until mixture thickens, about 3-4 minutes. Remove from heat and place plastic wrap directly on surface. Refrigerate until set.
08 - Place chopped chocolate, heavy cream, and butter in a microwave-safe bowl. Microwave in 20-second intervals, stirring between each, until smooth and glossy. Allow to cool slightly.
09 - Pipe or spread approximately 1 teaspoon of custard onto flat side of half the cooled cookies. Top with remaining cookies to create sandwiches.
10 - Spoon or pipe chocolate glaze over top of each cookie sandwich. Allow glaze to set completely at room temperature until firm.