Macerate the strawberries. Slice the strawberries however you like — I prefer pretty rounds, so I cut them on their side. Place them in a bowl and sprinkle ¼ cup of sugar over the top. Give them a stir and set them aside. They need at least 15–20 minutes for the juices to release and the strawberries to sweeten up. You can prep them up to 24 hours ahead of time, which makes this dessert wonderful for entertaining.
Make the stabilized whipped cream. In a mixing bowl, combine the heavy cream, powdered sugar, vanilla, and instant vanilla pudding mix. Using the whisk attachment on your mixer, beat until the cream holds its shape — this should take just 3 to 5 minutes total. The pudding mix is the little trick that keeps your whipped cream from drooping. It will hold beautifully for hours, which is perfect if you're serving this to company. Just be careful not to over-whip — stop as soon as it's thick and pillowy.
Mix the dry ingredients. Preheat your oven to 425°F. In a large bowl, add the self-rising flour and ¼ cup of sugar. Give it a quick stir to combine.
Grate the butter. Take your cold butter straight out of the fridge — don't let it warm up — and grate it directly into the flour using a box grater. This is the easiest way I've found to incorporate cold butter into biscuit dough. As you grate, sprinkle a little flour over the butter shreds so they don't clump together. Once it's all grated in, gently stir until the butter is evenly distributed throughout the flour.
Add the wet ingredients. Pour in the buttermilk, vanilla, and the egg (give the egg a quick whisk first). Stir gently — just until everything comes together. Don't overwork it. If you see a couple of dry pockets, add a small splash more buttermilk and stir a couple more times. Overmixing is what makes biscuits tough, and we want these light and fluffy.
Cut out the biscuits. Lightly flour a clean surface and turn the dough out. Pat it together with your hands and fold it 2 or 3 times — no need for a rolling pin. Pat the dough to about 1-inch thick. Dip your biscuit cutter in flour and press straight down — don't twist. Twisting seals the edges and keeps the biscuits from rising tall and flaky. Place the biscuits on a baking sheet just slightly touching, so they rise up rather than out. Gather and re-pat the scraps to cut out the rest.
Brush and sprinkle. Brush the tops of each biscuit with a little heavy cream — this gives them that beautiful golden color. Then sprinkle generously with sugar in the raw for a sweet, crunchy top.
Bake. Bake at 425°F for 12–15 minutes, until the tops are golden and the layers are tall and flaky. My oven runs a little fast, so mine were perfect at 12 minutes. Check yours a couple of minutes early just to be safe. Let them cool for 20 to 30 minutes before assembling — the strawberries and cream are chilled, and you don't want a warm biscuit to wilt them.
Assemble. Split each biscuit in half. Spoon or pipe a generous dollop of whipped cream on the bottom half, top with macerated strawberries (don't forget to drizzle some of that beautiful syrup over them), then add the top of the biscuit. Repeat the layers — more whipped cream, more strawberries — and serve right away.