Place the freeze-dried strawberries into a blender or food processor. Blend until a fine, powdery consistency is achieved. Reserve 1 teaspoon of this powder for the glaze if desired.

In a medium mixing bowl, whisk the remaining strawberry powder and all-purpose flour together until well blended.

In the bowl of a stand mixer fitted with the paddle attachment, cream the softened butter and powdered sugar on medium speed until light and fluffy, approximately 1 minute. Add the vanilla extract and mix until incorporated.

Gradually add the flour-strawberry mixture to the creamed butter and sugar. Mix on low speed until the dough forms a cohesive consistency. Avoid overmixing to maintain the delicate texture.

Shape the dough into a disc, wrap tightly in plastic wrap, and refrigerate for 15 minutes. This step ensures the dough is firm enough to roll and cut.

Lightly flour a clean surface and roll out the chilled dough to a thickness of ¼ inch. Use cookie cutters to shape the dough as desired. Place the cut cookies onto a parchment-lined baking sheet.

Transfer the baking sheet to the refrigerator for an additional 15 minutes. This prevents the cookies from spreading while baking.

Preheat the oven to 350°F (175°C). Bake the cookies for 15-17 minutes or until the edges are lightly golden. Allow them to cool on the baking sheet for 5 minutes before transferring to a wire rack.

While the cookies cool, whisk together powdered sugar and milk in a small bowl until smooth. Add the reserved strawberry powder for a pink hue and enhanced flavor, if desired.

Once completely cooled, drizzle the glaze over the cookies or dip the tops into the glaze. Optionally, sprinkle with crumbs of freeze-dried strawberries for decoration. Allow the glaze to set for about 15 minutes before serving.