Clean strawberries with water. Pat dry with paper towels. Chop strawberries into small pieces and then place in a medium bowl. Sprinkle sugar over strawberries then gently stir. Cover bowl with lid and let strawberries soak in sugar for at least 3 hours.
Preheat oven to 325 degrees F. Place 24 cupcake liners in cupcake pans.
Prepare cupcake batter according to package directions. Stir in vanilla extract. Divide batter evenly among liners. Using the 2 Tablespoons of granulated sugar, sprinkle a pinch of sugar over the tops of batter in liners before baking. Bake 15 minutes or until toothpick inserted in center comes out clean. Let cupcakes cool completely.
Take each cupcake and pour 1 Tablespoon of strawberry glaze over the top. Spoon 1 Tablespoon of fresh strawberries over the glaze. Top with fresh whipped cream. Repeat for all cupcakes. Serve and enjoy!