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The biggest problem in sleeping with wet hair is that when you toss around, your hair tangles... and when it's wet - it's extremely vulnerable to breakage. And if you put it up, it can break around the elastic. Satin or silk pillowcases help (but don't get expensive ones, because water can sometimes stain them) and if you do sleep w/ wet hair (or pull it up) lift it all up behind your head so that you really aren't laying on the ends. If you put it up, put the pony on the top of your head.