Slice the strawberries and put them in a large bowl. Sprinkle ¼ cup granulated sugar over the fruit. Toss gently to coat. Let the berries sit at room temperature for at least 30 minutes so they release their juices.

Preheat the oven to 425°F (220°C). Line a baking sheet with parchment paper.

In a large bowl, whisk together 2 cups of flour, ¼ cup sugar, 1 tablespoon baking powder, and ½ teaspoon salt. Cut in ½ cup cold butter until the mixture looks crumbly with pea-sized butter bits.

Pour in ⅔ cup whole milk and 1 teaspoon vanilla extract. Stir gently until the dough just comes together. Do not overmix; a few dry streaks are okay.

Use a large spoon to drop rounded spoonfuls of dough onto the prepared baking sheet, spacing them about 2 inches apart. Smooth tops slightly if needed.

Bake 12–15 minutes, until the shortcakes are golden on top and spring back when touched. Let cool a few minutes on the pan.

Chill a mixing bowl and beaters. Pour in 1 cup cold heavy whipping cream, add 2 tablespoons powdered sugar and 1 teaspoon vanilla extract. Beat until soft peaks form — do not overwhip.

Split each shortcake in half horizontally. Spoon macerated strawberries and their juices onto the bottom half. Add a generous dollop of whipped cream, then crown with the top halves. Serve immediately.