Preheat your oven to 350°F (175°C) to ensure even baking.
In a food processor, pulse the freeze-dried strawberries until they reach a fine powder consistency. Set aside.
In a large mixing bowl, beat the room temperature salted butter with granulated sugar using a hand mixer or stand mixer until light and fluffy.
Add the egg and 2 teaspoons of vanilla extract to the butter-sugar mixture. Beat until well combined.
In another bowl, whisk together the all-purpose flour, baking soda, kosher salt, and powdered freeze-dried strawberries.
Gradually add the dry mixture to the wet ingredients, mixing until just combined. Be careful not to overmix.
Using a cookie scoop or spoon, drop rounded tablespoons of dough onto a baking sheet lined with parchment paper, leaving space between each cookie.
Bake the cookies in the preheated oven for 10-12 minutes or until the edges are lightly golden. Let cool on the baking sheet for a few minutes before transferring to a cooling rack.
In a mixing bowl, beat the cream cheese until smooth. Gradually add the powdered sugar, hot milk, and 1 teaspoon of vanilla extract. Mix until creamy and well-blended.
Once the cookies are completely cooled, spread a generous layer of cream cheese frosting on top of each cookie. Drizzle some strawberry jam over the frosting for an extra touch.
Your Double Strawberry Sugar Cookies are now ready to be enjoyed! Serve them at a gathering or keep them all to yourself—they're that good!