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we had to retrain charlie twice after we first did at 4.5 months, but both times it only took one night. i think once was at 13 months and another around 16 months. the first time was due to milestones/travel/sickness all combined.

we sleep trained olive at 13 months then she was sick for 14-15 and had to retrain at 16 months. but she was relatively easy to train -- even easier than charlie, and i think he was pretty easy. she is 19 months now and so far so good!

As I wrote in your other thread, we're still in the process of this same method ourselves, but I have a few thoughts for you.

1. I was really worried about the retraining thing too, but after seeing how well they have really learned this sleep this as a new SKILL, I'm much less worried about it. And because we'll just plan to do a shorter version of the stay in the room method if they need some retraining/reminders, it's not as daunting to me as having to CIO every time. That said, my kids are 3.5 months older, so there is more developmental stages that they have already passed through, so we have fewer WWs left, etc. As far as listening to them cry, it's still not easy, but for me it was easier to be there with them crying than listen to them cry from another part of the house.

2. I really and truly thought that sleep training, even the sleep sense type might not work for my son. He is a very sensitive kid and has always wanted lots of snuggles, and we had coslept at least part of the night more often than not. He had 2 rough nights where he would fall asleep for a few minutes then wake up again right away, so we'd essentially be in there on and off for a 1.5-2 hours, and a few other times, but he did longer stretches of sleep mixed in with that, so it wasn't too bad. By night 3, he only needed me for 2 quick wakeups (5 min each), and nights 4 and 5, he has STTN! Even using the program, I figured he'd still have a couple of night wakeups just because of his personality, but he has proved me wrong!

And even in less than a week's time, both kids already seem happier, and so are DH and I. I wasn't sure how it was all going to play out, but we decided to give it an honest try, and my biggest emotion through all of this? Immense pride in my kids at how quickly and fantastically they have made this transition and bettered our family life for it.

My experience has been that we've had to re train at times, especially after sickness and vacation, but I don't like to call it re training, because it sounds negative. Instead I just look at it as helping LO to remember his soothing and falling asleep skills. Plus, my son is 2.5, we've had a rough time of sleep. He's not textbook in any sense of the word.