We had a very simialr situation with our 18 month-old daughter. She did good in the toddler bed at first, but it slowly got worse and worse. It ended up where it was taking an at least an hour to get her down and she was waking up several times a night sometimes for hours at a time, then still getting up at 5:30. No body was getting ANY sleep. We tried the suppernanny technique, but it was a game to her. She would just keep coming back out with a big smile on her face. We ened up putting a baby gate in her doorway. I was originally opposed to the idea, but I was at my wit's end. Now, i think it was the best thing we could have done. We had to let her cry it out again. We used the Feber Method, where you slowly increase the amount of time that you let them cry. I had to physically put her back into bed each time, and eventually she just stayed. It worked wonders!!! Now she only crys for a few minutes if that. She is asleep by 8:30 and isn't up again until after 7. WE are all much happier people. The most important thing is to be consistent though. I knew that if I gave in once to the crying (it was REALLY hard not to) she would cry longer and harder in the future, hoping that I would rescue her again. Godd luck with your little guy. It will pass.