Preheat the oven to 325 degrees F and line baking sheets with parchment paper. In a food processor, pulse together the freeze dried strawberries until a powder consistency forms. It's ok to have large bit size pieces.
In a large mixing bowl with an electric mixer or in the bowl of a stand mixer with a paddle attachment, cream the butter and powdered sugar together until combined and smooth.
Add in vanilla extract, milk, freeze-dried strawberry powder (reserve 1 tablespoon for the icing).
Add flour and continue to beat until combined and strawberry shortbread cookie dough has formed.
Roll out cookie dough ball into a circle, 1/4 inch thick with a rolling pin on a lightly floured surface, you could also use powdered sugar instead. Cut out cookies with a 2-3 inch heart cookie cutter (or any favorite cookie cutter) and place on prepared cookie sheets. Bake cookies for 12-15 minutes or until the edges are a light golden brown. Let cookies cool for 5 minutes before transferring to a cooling rack to cool.
In a small bowl, whisk together the powdered sugar, vanilla extract, milk and strawberry powder together until smooth. Add more powdered sugar if its too thin, and more milk if it’s too thick.
Once the cookies have cooled, drizzle the tops or frost the whole cookie with the strawberry glaze and let sit for a few minutes to set. Enjoy!