01 - Preheat oven to 350°F. Lightly grease a 24-cup mini muffin tin with cooking spray or butter.
02 - In a medium bowl, whisk together flour, baking soda, and salt until evenly blended.
03 - In a large bowl, beat softened butter and granulated sugar with electric mixer on medium speed until light and fluffy, approximately 2 minutes.
04 - Add egg and vanilla extract to butter mixture. Beat until fully incorporated, scraping down sides of bowl as needed.
05 - Gradually add dry ingredients to wet ingredients, mixing on low speed just until combined. Do not overmix.
06 - Scoop approximately 1 tablespoon dough into each muffin cup. Press gently with fingers to form cup shape, pushing dough up sides of tin.
07 - Bake for 10 to 12 minutes until edges are lightly golden. Centers should still be slightly soft.
08 - Remove from oven. While still warm, gently press center of each cookie with back of spoon to deepen cup shape. Cool in tin for 10 minutes.
09 - Carefully transfer cookie cups to wire rack. Cool completely before filling.
10 - In chilled bowl, whip heavy cream, powdered sugar, and vanilla with electric mixer until stiff peaks form.
11 - Fill each cooled cookie cup with whipped cream. Top with fresh berries, sprinkles, or mini chocolate chips as desired.