Preheat your oven to 325°F. This will ensure it’s at the right temperature when you're ready to bake the phyllo cups. While the oven heats, grease the cavities of a mini muffin pan lightly with butter or cooking spray to prevent sticking. Set the pan aside.
On a large cutting board, lay out a single sheet of phyllo dough. Using cooking spray or melted butter with a pastry brush, lightly coat the entire sheet. Layer another phyllo sheet directly on top, and repeat the spraying or brushing process. Continue layering and coating until you have 5 sheets stacked together, creating a single, multi-layered sheet.
With the layered phyllo sheets ready, use a pizza cutter to cut the dough into 12 equal squares. You can measure slightly if needed to make sure the squares fit neatly into the muffin pan.
Carefully take one square at a time and press it gently into the cavity of the greased mini muffin pan. Use your fingers to shape the dough so it covers the bottom and sides evenly. Be gentle to avoid tearing the dough. Repeat this process for all 12 cavities.
Place the prepared muffin pan in the preheated oven and bake for about 10 minutes, or until the phyllo cups are golden brown and crispy. Remove the pan from the oven and let the cups cool completely.
While the phyllo cups are baking, wash and dry your strawberries. Cut them into very small chunks and place them in a mixing bowl. Sprinkle the chopped strawberries with sugar and stir until the sugar is evenly distributed. Cover the bowl and refrigerate to let the flavors meld while the phyllo cups cool.
Once the phyllo cups are completely cool, gently remove them from the muffin pan. Fill each cup with a spoonful of the prepared strawberry mixture. Be sure not to overfill, as you’ll need room for the topping.
Just before serving, top each strawberry-filled phyllo cup with a dollop of whipped cream. For an extra touch, you can garnish with a small strawberry slice or a mint leaf.
Arrange the assembled strawberry shortcake pie bites on a serving platter and enjoy. These are best served fresh to maintain the crispness of the phyllo cups.