Slice strawberries and toss with sugar. Let them rest at room temperature for at least 20 minutes. This process, called maceration, draws out juices and concentrates flavor.

In a bowl, whisk flour, sugar, baking powder, and salt. Cut in cold butter until the mixture resembles coarse crumbs. Add milk and vanilla, mixing just until combined. Overmixing leads to dense shortcakes.

Turn dough onto a lightly floured surface and gently pat into a thick round. Cut into portions and place on a lined baking sheet. Bake until lightly golden and cooked through.

Whip heavy cream with powdered sugar and vanilla until soft peaks form. Stop early rather than late; overwhipped cream becomes grainy.

Split shortcakes in half. Spoon strawberries and juices over the bottom half, add whipped cream, then top with the remaining shortcake.