Place the freeze dried strawberries in a high speed blender or food processor and pulse until they are a fine crumb — similar to the texture of powdered sugar.
(Optional) Remove 1 teaspoon of the strawberry powder and set it aside for the glaze later. Feel free to skip this step if you would prefer a plain glaze.
Place the remaining strawberry powder in a medium bowl. Add the flour and whisk to combine.
Add the butter, powdered sugar, and vanilla to the bowl of a stand mixer fitted with the paddle attachment (or to a large bowl if using a hand mixer). Beat on medium speed until the mixture is light and fluffy — about 1 minute.
With the mixer on low speed, slowly add the flour-strawberry mixture.
Once fully combined, scrape down the sides of the bowl and mix for just a little bit longer to make sure no large lumps of flour remain.
Shape the dough into a disc and wrap it tightly with plastic wrap. Place it in the fridge to chill for 15 minutes.
Turn the dough out onto a lightly floured surface and roll it to ¼ inch thick. Cut out your desired shapes and sizes and place them on a baking sheet lined with parchment paper.
Place the baking sheet in the fridge to chill for an additional 15 minutes. While the cookie dough chills, preheat the oven to 350 degrees F.
Bake the cookies for 15 to 17 minutes, or just until the centers are set. You don’t want them to brown too much!
While cookies are baking, prepare the glaze by whisking together the powdered sugar and milk. Add the optional reserved teaspoon of freeze dried strawberry powder, if using.
Drizzle the glaze over the cooled cookies (or dip the cookies into the glaze) and garnish with additional freeze dried strawberry crumbs, if desired. Allow the glaze to set completely before storing — about 15 minutes.
Store these cookies in an airtight container at room temperature for up to 3 days.
This nutrition information is based on the exact products I used in this recipe. Brands and sizes of products could alter exact nutrition and should always be calculated independently.