Preheat oven to 400°F. Line a baking sheet with parchment paper.
In a large bowl, whisk flour, sugar, baking powder, and salt. Using a pastry cutter or your fingers, cut in butter until the mixture resembles coarse crumbs.
Stir in milk and vanilla until the dough comes together. Turn dough out onto a floured surface and pat into a 1/2-inch-thick disc. Use a round biscuit cutter to cut out 8 shortcakes. Place on prepared baking sheet.
Bake for 12-14 minutes or until golden brown. Let cool completely.
Strawberries
In a medium bowl, toss sliced strawberries with sugar. Set aside.
Cheesecake
In a large bowl, beat cream cheese, powdered sugar, and vanilla until smooth. In a separate bowl, beat heavy whipping cream until stiff peaks form. Fold whipped cream into the cream cheese mixture.
To assemble, slice cooled shortcakes in half. Spread the cheesecake filling on the bottom half and top with strawberries. Replace the top half of the shortcake. Serve immediately.