If you're having a hard time getting it to thicken then you should probably scald the milk first before putting it in with the dry ingredients. Scalding the milk helps kill off enzymes that prevent it from thickening in food. Also, use milk that at least has some fat in it. If you use skim milk or milk substitutes, that probably contributes to the problem of soupiness. I used low fat milk, and it worked fine. Mine is not so soupy and stays up for the most part when I cut a slice, but the sides do cave in a little, however I did use a recipe that is exactly like this one in every way except that it used THREE cups of milk, so if I had used just two like this recipe calls for then I imagine it would be more solid. I also let it sit in the fridge overnight so it had a lot of time to set. Besides that, I tried to make it a little healthier by using 1/2 cup organic pure cane and 1/4 cup brown sugar instead of white sugar, unbleached flour, earth balance instead of butter, and low fat milk. I'm not sure if any of that helped or hurt the consistency of the filling, but it turned out okay in my opinion. Also, I pureed a couple of bananas in the blender and mixed it in with the pudding to make it more banana-y and it tasted DELICIOUS! Even with all the substitute ingredients it tasted just like store bought pudding. However, because of the sugar I used, the outcome was more brown then yellow. It was still yummy, but not as pretty. It's easy to look past if you want to be healthier.
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If you're having a hard time getting it to thicken then you should probably scald the milk...