Preheat the oven to 400°F and line a baking sheet with parchment paper. Chill a medium bowl, or the bowl of your stand mixer, in the refrigerator.

Prepare the strawberries: In a large bowl, toss the strawberries with the sugar until the sugar dissolves. Set aside to macerate while you prepare the biscuits and whipped cream.

Make the biscuits: In a large bowl, whisk together the flour, sugar, baking powder, and salt. Add the cold butter and toss to coat. Use your hands or a pastry cutter to work the butter into the dry ingredients until the mixture resembles a coarse meal. Add the milk and mix with a wooden spoon or spatula until a shaggy dough forms. Knead with your hands to incorporate any remaining dry flour.

Turn the dough out onto a lightly floured surface. The dough might be slightly sticky—that’s ok. If it’s too sticky to handle, knead in a little more flour. Pat or roll the dough into a 1/2-inch-thick rectangle. Fold the dough into thirds and pat or roll again until 1/2-inch thick. Rotate a quarter turn and fold into thirds again.

Pat or roll into a 1/2-inch-thick rectangle, then use a sharp knife to cut the dough into 6 square biscuits. Place the biscuits on the baking sheet. Lightly brush the tops with milk and sprinkle with sugar.

Bake for 15 to 20 minutes, or until golden brown around the edges. Transfer to a wire rack to cool.

Make the whipped cream: Combine the cream, powdered sugar, and vanilla in the chilled mixing bowl. Using a stand mixer or electric mixer fitted with a whisk attachment, whisk on low to incorporate the powdered sugar into the cream. Increase the speed to medium and beat for 4 to 8 minutes, or until medium peaks form.

To serve, slice the biscuits in half crosswise and fill with some of the macerated strawberries and whipped cream. Top with more whipped cream and/or strawberries, as desired.