Okay, both my boys had this problem when they were about 3 years old (they are now both almost 7 and 4). I thank God everyday that I came across a doctor who knew what to do other than offer a prescription. First of all, I think some kids are just more sensitive to foods containing white flour and simple sugars. When they were in daycare it seemed there was a party everyday for something and the kids were getting cookies and cupcakes, etc. Inevitably, this had a negative impact on their BM's. This doctor said I had to really watch their diet and improve their fiber. AND make sure they gets lots of liquid. The bowel (or I guess the intestines), actually absorbs water from your body to help move waste out. And as you've read already, increase the fiber. There are so many great food products out there with added fiber that don't have all the preservatives and gunk. Of course, good ole apples and grapes helped my little guys a lot and they were less expensive! ALSO, keep in mind that calcium (milk, yogurt, cheese) hardens stools, as do bananas and carrots. Our children still need these things, but not in huge quantities. At the time, my kids LOVED milk and that wasn't helping matters. Of course,they make calcium fortified OJ now, so we drink that too. And in the end, your child has to WANT to poop. I offered incentives, especially with my youngest. He finally got to watch his Barney video, we had a pizza party at Cici's AND he got something else that I can't remember. And then of course, my boys were scared. Maybe it was the pressure in their bottom, or pain or the great unknown...but with my oldest, when he was 3, I told him (and I know this sounds insane) that his poops wanted out to see their families. And when his bottom hurt, it was because they were getting sad that he wouldn't let them out. And that if he would just poop they'd be happy and his bottom would feel so much better. I don't know what made me say it, but it actually worked with both of them. They felt like they were helping and doing a good thing. Of course, they've outgrown the whole 'family' concept. In addition, I will add, that I keep Miralax on hand. If I see a problem arising, like lots of sweets for a special occasion or maybe we've been busy and I've not gotten enough liquids to them and if they haven't had a BM for one day, then I mix some in a drink. I always make sure they have a BM once a day. My 3 year old gets so busy, I'm sure he holds it. I almost always have to remind him by late afternoon that he needs to go and he will. Of course, I take this as a sign to increase fiber and liquid too. Miralax, apparently, is such a hit because it doesn't get absorbed into the body. As horrible as it sounds, I think it's like a form of plastic that slicks the intestines and comes right out with the waste. It's harmless, but I still don't like giving them a whole lot. And it really takes a good 2 or 3 days to work, so I always try to do the liquid, fiber, etc. Remember, you are not alone. It was terribly painful to see my children so miserable. You'll be fine and so will he. It takes a real commitment of time and effort to get him through it initially, but it will get much easier and you'll be glad for it. So don't lose hope, get him back into some big boy underwear and tell him you're going to help him be a big boy. Sometimes I even held their little hands while they sat and pushed. They'd just squeeze, squeeze, squeeze my hands, and push so hard I thought their little eyeballs would pop out. :-) But they did it and afterwards they got lots of verbal praise and kudos (plus their prizes) and I think they really felt like they accomplished something. Good luck!