Hello k_lachenman, There are many factors that influence the longevity of bonding, especially on anterior(front) teeth. Typically what I find is that it has a lot to do with the surface area of the chip or fracture. The larger the chip(more surface area present) the better the bond and typically these will last longer. There are a few tricks we as dentists can do to increase the surface area for bonding when preparing a tooth for a restoration but I won't go into details. When you get into fairly large fractures, however, a crown is usually the best restoration of choice. Typically bonding on the front teeth will break off more easily than natural tooth structure and have to be redone quite often. This is why we always mention to patients to be careful when biting into things after a procedure such as this is done. The only reason I can think of as to why it falls off when he is asleep is that he is doing something during the day to weaken the bond or break it off almost entirely and then it just finally gives way when he is asleep. He may be grinding his teeth at night as well, which could definitely break off the bonding. Maybe explore your options for a nightguard after he gets them fixed again?? I believe that may help until he is older and can get a crown done that will last him a while. Hope it helps-Christopher Cassidy DMD