Combine strawberries with sugar and vanilla; mash slightly. Let stand at least 30 minutes, tossing occasionally.
Preheat oven to 400°. For shortcakes, whisk together flour, 4 tablespoons sugar, baking powder, baking soda and salt. Cut in butter until crumbly. Add buttermilk; stir just until combined (do not overmix). Drop batter by 1/3 cupfuls 2 in. apart onto an ungreased baking sheet. Brush with 2 tablespoons heavy cream; sprinkle with remaining 1 tablespoon sugar. Bake until golden, 18-20 minutes. Remove to wire racks to cool completely.
For topping, beat heavy whipping cream until it begins to thicken. Add sugar and vanilla; beat until soft peaks form. To serve, cut shortcakes in half; top with strawberries and whipped cream.
Test Kitchen Tips: Secret to Tender Shortcake: Make sure the butter is cold and cut it in until it’s about the size of peas. As it melts during baking, this will create the small air pockets that give the biscuit its flakiness. Golden Brown Goodness: Brushing the biscuit tops with cream helps the sugar stay in place as well as giving the top a rich golden brown color when it's baked. Bump up the Biscuit: Stir grated lemon zest, orange zest or a bit of spice such as ground cardamom into the biscuit mixture. Add a pinch of cinnamon and nutmeg to the sugar on top. Don't Have Buttermilk?: Place a tablespoon of white vinegar or lemon juice in a measuring cup and fill with regular milk to reach the 1 cup mark. Swap the Fruit: Add fresh herbs or a favorite liqueur into the strawberry mixture, or substitute sliced mangoes, or peaches and blueberries, for the strawberries. Whip Smart: It’s important the heavy cream is cold when you mix it—you’ll get more volume. Start out on low speed and be patient. You can make the whipped cream up to 2 hours ahead, then gently stir to reincorporate when you’re ready to serve it. Perfect Berries: Avoid mashing the strawberries too long or they will become mushy.
1 shortcake with 1/2 cup strawberries and 1/3 cup whipped cream: 638 calories, 36g fat (22g saturated fat), 102mg cholesterol, 710mg sodium, 72g carbohydrate (33g sugars, 4g fiber), 9g protein.
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