My 2 year old has a few weeks on end that she will sleep through the night but is not a real good sleeper and hasn't ever really been. Some of the things that have worked for us include making sure she gets some extra milk before bedtime to help her feel full longer. She usually goes down around 8:30 and will sleep until 6:30 and we can live with that! When I know she has been teething and she would wake up in the middle of the night, I would put some Orajel on her teeth, turn on her music, and she would usually go right back to sleep. If your little one is teething, you can try some Tylenol or Motrin at bedtime. If he wakes up after it has worn off, you can give another dose per the instructions on the medicine. My daughter has had a really hard time teething. Rubbing some olive oil on his gums can make that easier and you may not need the Tylenol or Motrin. There are times when she wakes up for no reason and doesn't want anything - despite her list of things that she says she wants - and we have had to let her cry. She has cried for as long as an hour before but there was no harm done and she eventually went back to sleep. Most of the time if she wakes up, I can turn her music on, cover her back up, and she is content to go back to sleep with no fuss. I do agree with the mom that said he doesn't really need the milk. I had the same problem with my daughter at that age and I talked to my pediatrician about it. She told me not to give her the milk, she didn't need it, and she just needed to go back to sleep. She gave me some of the tips here. I do put a sippy cup of water in my daughter's bed and she will help herself, get a drink, and I never hear a peep out of her. You may have to try several things before you find what will work with your little one but it is certainly worth the effort. And I don't think that any of this is about what is "convenient" for you. If your little one isn't sleeping, you aren't sleeping, and a tired parent can make mistakes that can be dangerous for your child. Good luck!