In a medium saucepan, whisk together the granulated sugar, cornstarch, and salt.
Gradually add the milk to the dry ingredients, whisking continuously until smooth.
Place the saucepan over medium heat and continue to stir until the mixture thickens and begins to bubble, about 5 minutes. Once thick, remove from heat and stir in the vanilla extract.
Transfer the pudding to a mixing bowl and cover it with plastic wrap, pressing it directly onto the surface to prevent a skin from forming. Allow it to cool for 10 minutes.
In a separate bowl, whip the heavy cream with powdered sugar until soft peaks form.
Once the pudding has cooled, begin assembling the cups by adding a layer of pudding to each dessert cup.
Follow with a layer of whipped cream, then an optional layer of crumbled cookies or graham crackers.
Repeat the layers until you reach the top of each cup, finishing with a layer of whipped cream.
Top each cup with an assortment of Easter candies.
Refrigerate for at least 1 hour to set before serving.