Creating Strawberry Shortcake Cups is simple if you adhere to these clear steps:

1. Macerate Strawberries: In a bowl, combine the chopped strawberries, 1/4 cup granulated sugar, and vanilla extract. Let them sit for 10 minutes to release their juices.
2. Preheat Oven: If you're baking the cake, preheat your oven to 350°F (175°C).
3. Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, 1/4 cup sugar, baking powder, and salt.
4. Combine Wet Ingredients: In another bowl, mix the milk, vegetable oil, and egg until fully combined.
5. Combine Mixtures: Gradually add the wet ingredients to the dry ingredients, stirring until smooth. Avoid overmixing.
6. Bake: Pour the batter into an 8×8-inch baking dish or cupcake liners and bake for 15-20 minutes or until a toothpick comes out clean. Remove from the oven and allow to cool.
7. Whip Cream: In a chilled bowl, beat the heavy whipping cream until soft peaks form. Sweeten with sugar if desired.
8. Assemble Cups: Once the cake is cool, cut it into cubes. In serving cups or bowls, layer the cake cubes, macerated strawberries, and whipped cream.
9. Repeat Layers: Continue layering until the cups are filled, finishing with a dollop of whipped cream on top.
10. Serve Immediately: These are best enjoyed right after assembling for optimal freshness.

The straightforward process ensures that even beginner bakers can achieve this delightful dessert without difficulty.