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Sleep is the hardest thing about parenting for me and I'm definitely not in a position to be giving advice! We sleep trained around 7/8 months and I was so worried about what we would do if he woke up- which obviously he did! We did comfort/soothe which sometimes meant holding him in a chair while he slept. And he did go back to STTN. How often is he waking? How many days has it lasted? A few times it was for teeth and we would give him Motrin which seemed to help. But sometimes he just needed some extra love. My son is 21 months and we haven't "retrained" him. Good luck!

@Goldengirl: we didn't have an 8 month regression (at least nothing discernible) but of course after we sleep trained at 4/5 months we still had occasional wake ups. Let's say once a month. And then around 18 months we had a legit regression.
I went in and soothed him at every random wake up and every regression wake up (18 month regression lasted almost 2 months!) and I never had to retrain. He always went back to sleeping through the night without crutches, no re-training needed.
I would give something a good 3-4 weeks before I'd determine that it's a new habit that needs retraining vs a regression. I knew my sons 18 month regression was only a regression the whole 2 months because it wasn't every night (maybe 3-4 nights a week) and with a quick 5 min or so rocking he went back in the crib drowsy but awake and didn't wake up again. Slowly it became less and less, which also clued me in that it was a regression and not some bad habits from me soothing him.

Long way of saying - I think that once they are trained, as long as the soothing is within a reasonable realm (some rocking and shushing till drowsy but awake vs rocking or feeding back to sleep) they will go back to their normal "trained" sleep habits once the regression passes.
And I think you'll know once it gets to the point of "ok we need to retrain" vs "this is still the regression".
Am I making sense?

Like @justjules: , we had to re-sleep train multiple times, and it never lasted very long... just about a month each time. We sleep trained at 5m, 8m, and 10m. We did have some major external changes in there, too: going to childcare, moving from our room to the nursery, 10-day cross country trip, etc.

Xmas travel ruined him and he was up multiple times a night, 11-12months. But then he just started STTN at 12mo through no effort on our part and it's been good since.

@Goldengirl: so glad it helps! I wasn't sure if it was what you were looking for. As time goes on, if you need anything else just tag me I'll do my best to help.
I'm very passionate about infant/toddler sleep!

My kids have both gone through periods after sleep training where they would wake and cry a bit. With my oldest, we would generally give her 10-15 min and see if she'd settle before going in, unless we knew or suspected she was sick. I always tell people that she never had any regressions and we never had to sleep train again, but I suspect that we just nipped any potential bad habits in the bud by doing a mini version of CIO every so often. She was always pretty good though, and wasn't one to cry for like an hour straight. We definitely never needed to do a full-on sleep training after the first time.

My 8 month old has been less consistent and it seems like he has a little regression every 2-4 weeks where we need to let him CIO, sometimes for a longer time than I'm really comfortable with (like 30-40 min). I hate doing it, but he seems to need it because when we go down to soothe him, he ends up wanting to sleep on us and gets angry when we put him in his crib. The good news is that because we've been consistent, his sleep has been better and better, and he slept through the night months earlier than his big sis did. He recently was sick and of course we threw everything out the window (rocked him and held him all night and let him co-sleep), and I was happily surprised when he went right back to STTN once he was better again.

So I guess, I don't really call it re-training, but I suppose our strategy has been to allow them to cry when they need it. It worked so well for our almost 4 year old, who is a rock star sleeper, and so I'm hoping for the same with the little guy.

@Goldengirl: Have you tried just leaving? That is a situation where I just walk away, and my guy usually settles himself within 5-10 min.

@Goldengirl: That's tough. I'd probably give him a bit more time. My guy does this every so often and it sucks to let him cry but then he's usually back to normal the next day, so I always feel like it's worth it.

@Goldengirl: I would start by challenging yourself to wait 15min to see if he settles down at all. It's hard! But often E settles after about 15min. What was the hardest for me was that if he was still super upset after those 15min and I went in, if I was just training him to cry for 15min and then mama will come. It all worked out in the end for us, though.