Beat the softened cream cheese, powdered sugar, and vanilla until completely smooth. Scoop into 18 small mounds (about 1 rounded teaspoon each) onto a parchment-lined plate. Freeze for at least 30 minutes until firm.
In a large bowl, cream the softened butter, brown sugar, and granulated sugar until light and fluffy, about 2–3 minutes. Beat in the egg, egg yolk, and vanilla until combined.
In a separate bowl, whisk together the flour, graham cracker crumbs, baking soda, and salt. Add the dry ingredients to the butter mixture and mix on low just until a soft dough forms. Gently fold in the chopped fresh strawberries and freeze-dried strawberries. Cover and chill the dough for 15–20 minutes so it firms slightly.
Preheat oven to 350°F. Line baking sheets with parchment paper. Scoop about 2 tablespoons of dough and flatten it slightly in your palm. Place one frozen cream cheese mound in the center. Wrap the dough around the filling, pinching to seal completely so no cream cheese is exposed. Roll into a smooth ball and place on the baking sheet, spacing 2 inches apart. Chill the shaped cookies 10–15 minutes if the dough has softened.
Bake one sheet at a time for 12–14 minutes, until the edges are set and lightly golden. The centers will still look soft. Let the cookies cool on the baking sheet for 5–10 minutes—they firm up as they cool—then transfer to a wire rack.
