01 - Preheat oven to 400°F. Line baking sheet with parchment paper.
02 - In medium bowl, whisk flour, sugar, baking powder, and salt. Cut in cold butter with pastry cutter until mixture resembles coarse crumbs.
03 - Stir milk and vanilla into flour mixture until just combined. Do not overmix.
04 - Drop tablespoon-sized dough mounds onto baking sheet. Bake 12-15 minutes until golden brown. Cool completely.
05 - Combine sliced strawberries, sugar, and lemon juice in bowl. Toss gently and let sit 15 minutes to macerate.
06 - Beat cold cream, powdered sugar, and vanilla on medium-high speed until soft peaks form.
07 - Crumble shortcakes into bite-sized pieces. Layer in 4 glasses: shortcake crumbles, macerated strawberries, whipped cream. Repeat layers, finishing with whipped cream and strawberry garnish.
08 - Serve immediately or refrigerate up to 2 hours before serving.