Stir the orange gelatin into the boiling water until fully dissolved. Add the cold water and set the mixture aside to cool slightly until it thickens to a syrupy consistency.
In a separate bowl, fold the vanilla pudding together with 1 cup of the whipped topping and the vanilla extract until smooth.
Place a few pound cake cubes in the bottom of each of four clear cups. Add a few orange segments on top of the cake.
Spoon a layer of the thickened orange gelatin over the fruit. Follow with a layer of the pudding and whipped topping mixture.
Repeat the layers once more, ending with cake and orange segments if space remains. Finish each cup with a dollop of the remaining whipped topping and a sprinkle of orange and black sprinkles.
Chill the cups for at least two hours before serving so the layers set.