Start by making the pudding. Combine the canned coconut milk, milk beverage, tapioca flour, and cane sugar in a large saucepan.
Heat the mixture over medium heat, whisking constantly. Continue to whisk and heat until the mixture starts to thicken and is just starting to boil. This may take 10-12 minutes.
Once the mixture has just reached a boil, remove it from the heat. Stir in the vanilla extract and natural yellow food coloring. Transfer the pudding to a glass container. Allow the pudding to cool to room temperature, then cover it and put it in the fridge. Allow the pudding to set up in the fridge for at least 4 hours or up to overnight.
When you are ready to assemble the pudding cups, make the stabilized whipped cream. Chill a medium mixing bowl and your beaters in the freezer for 10 minutes.
Place the cream cheese in the chilled bowl and beat on low speed until it is creamy. Add the cocowhip and beat until combined, fluffy, and stiff peaks form, about 1-2 minutes. If the whipped cream is still not holding its shape, chill it in the fridge for 1-2 hours.
To assemble the pudding cups, measure out about 1/2 cup of cookie crumbs into the bottoms of 4 small glasses. Slice the ripe bananas and place several slices in each glass.
Give the pudding a good whisk to loosen it up and smooth out any clumps. Then divide the pudding between the 4 glasses.
Top the pudding cups with the stabilized whipped cream, more banana slices, and the whole gluten-free cookies. Serve immediately!