With the mixer on medium speed, add in the eggs one at a time mixing until fully combined. Add in the vanilla extract with the last egg.
Remove the mixing bowl from the stand mixer and add in the freeze dried strawberries and crushed Oreos. Using a rubber spatula, fold everything together until just combined. Cover bowl with plastic wrap and refrigerate for 3 hours.
Measure out 2.5 oz of dough per cookie. Lightly roll the dough into balls using the palms of your hands. Smooth out any cracks. Place the dough balls on a wax paper lined plate and place in the fridge uncovered to firm up, about 10 to 15 minutes while the oven preheats.
Bake cookies for 12 – 14 minutes. Remove the cookies from the oven halfway through baking and firmly tap the baking sheet on a heatproof surface to deflate the cookies. Rotate the baking sheet and return cookies to the oven and continue to baking.
For the strawberry crunch topping, combine the Oreo cookies, freeze dried strawberries, sugar, vanilla, and salt in the bowl of a food processor. Slowly stream in the melted butter and pulse the mixture until you reach pea sized crumbs. Top the cookies with the strawberry crumble.
For the vanilla glaze, In a medium size bowl, whisk together the powdered sugar, vanilla extract, and heavy cream until smooth.