Place strawberries in a bowl and stir in 1/4 cup sugar. Refrigerate until sugar has dissolved, about 30 minutes.

Preheat the oven to 400 degrees F (200 degrees C).

Place flour, remaining 1/4 cup sugar, baking powder, and salt in a large bowl. Cut butter into 8 pieces and add to the bowl. Cut butter into flour mixture with a pastry cutter or 2 knives until finely crumbled. Add milk and stir until dough just comes together.

Place dough on a lightly floured surface and turn to coat with flour. Fold dough in half, press down, and push forward with the heel of your hand. Turn 90 degrees. Repeat 12 times.

Roll dough out to 1/2- to 3/4-inch thickness. Cut into 4-inch circles with a ring cutter or a cookie cutter. Place shortcakes on an ungreased baking sheet.

Bake in the preheated oven until golden brown, 12 to 15 minutes. Remove from the oven and let cool slightly.

Pour heavy cream into a large bowl and beat with an electric mixer until increased in volume, but is still soft. Add confectioners' sugar and mix to combine.