Hull and slice the strawberries into 1/4-inch thick rounds, then place them in a bowl and toss with sugar. Let them sit for 15 minutes at room temperature—this allows the strawberries to release their juices and create a naturally sweet, syrupy base that will soak into the cake layers and prevent the dessert from drying out.

While the strawberries macerate, hand-tear the angel food cake into 1-inch pieces—tearing rather than cutting creates irregular edges that absorb the strawberry juices better than neat cuts would. In a separate small bowl, gently fold the vanilla extract into the whipped topping until evenly combined. I prefer using Cool Whip for this dessert because its sturdier texture holds up better in jars over time compared to fresh whipped cream.

Start with the vanilla whipped topping mixture from Step 2, placing about 2 tablespoons in the bottom of each 8 oz mason jar. Add a layer of cake pieces (roughly 2-3 tablespoons per jar), then top with strawberries and their accumulated juices (about 3 tablespoons). Repeat the layering sequence—whipped topping, cake, strawberries—until you reach near the top of each jar, then finish with a final layer of whipped topping and top with the most attractive strawberry slices for presentation.