In a medium mixing bowl, whisk pudding mix with 1 cup milk for 2 minutes. Chill 5 minutes.

In a separate large bowl, beat cream cheese with powdered sugar and vanilla until smooth, about 1-2 minutes. Add pudding to cream cheese mixture and beat to combine. Using a silicone spatula, gently fold in 1 tub of cool whip and ¾ cup of the toasted coconut, keeping as much air as possible in the mixture. Cover and refrigerate.

In a medium saucepan, melt butter. Add brown sugar and bring to a boil. Add drained pineapple, stirring gently. Mix cornstarch with reserved pineapple juice and add to simmering sugar mixture. Bring back to a boil and cook until mixture thickens. This mixture will continue to thicken as it cools. Pour into a bowl and let cool for at least 10 minutes. Place in the fridge or freezer to speed up cooling, if needed.

In a clear, deep sided dish; layer cake cubes, pineapple mixture, and cream cheese mixture, repeating layers to the top of the dish. Garnish the top with pineapple, toasted coconut, and maraschino cherries. This desert can be eaten right away, but will benefit from at least an hour of chill time.