Wash and dry the strawberries, remove the stems and leaves, then slice into bite-sized pieces (or dice into small chunks if preferred). Set 4 slices of strawberry aside for garnish.

In a small bowl, combine the strawberries with 2 tablespoons of powdered sugar. Cover the bowl and set aside.

In a medium mixing bowl, beat together the heavy whipping cream, 2 tablespoons powdered sugar, and the vanilla extract with an electric mixer on medium speed until stiff peaks form.

Slice the poundcake into ¾-inch cubes.

Place 4 plastic 9-ounce punch cups on the counter or on a cookie sheet.

Scoop half of the strawberry mixture evenly into the bottom of the cups.

Add about 4-5 cubed of the poundcake over the strawberries.

Scoop 3 tablespoons of the freshly made whipped cream over the poundcake in the cups.

Add the remaining strawberries evenly over the whipped cream layer.

Place 4-5 cubes of poundcake on top of the strawberries.

Top each cup with 2 tablespoons of whipped cream and a slice of strawberry as garnish.

Serve the strawberry shortcake cups immediately or chill for up to three hours before serving.