Begin by slicing your fresh strawberries and placing them in a medium bowl. Sprinkle half a cup of sugar evenly over the strawberries and gently toss to coat. Allow the mixture to sit for about 30 minutes at room temperature.

In a large mixing bowl, combine the instant vanilla pudding mix with three cups of milk. Use a whisk to blend the ingredients together until the mixture thickens, about 2 minutes.

Grab a clear trifle bowl. Start with a layer of cubed pound cake, followed by a layer of creamy vanilla pudding, and then a layer of macerated strawberries, spooning some syrup over the top. Repeat these layers two more times, finishing with strawberries.

Spread an 8-ounce tub of Cool Whip over the top of the trifle using a spatula. Garnish with fresh strawberries if desired.

Cover the bowl with plastic wrap and refrigerate for at least 4 hours, or up to 24 hours before serving.