Bedtime struggles

Stuck in a rut of LO taking 30-45 minutes if not more to fall asleep at night. We sleep trained around 7 months and he did so well for so long, fell asleep within 5-10 minutes with minimal fussing. Now for over a month it seems he’s been struggling to fall asleep. We’ve gone back to our sleep training strategies; putting him down, giving it 5 minutes, 10 minutes and so on. He naps (and goes down for naps) so well, it makes it so frustrating at bedtime. He naps about 1.5 hours in the morning, and 1.5 hours in the afternoon, with 3ish hour wake windows, a little longer before bed (we start the bedtime routine around the 3 hour mark). We’ve tried moving bedtime up, pushing it back, shortening morning nap, wake him up from naps so he doesn’t sleep too long. Once he does fall asleep, he almost always sleeps thru the night - except for the few times we’ve dealt with teething. I’m getting completely worn out and frustrated by this. Please send help.
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I peeped your profile. It shows your LO is 10 months. That's right around the time they start getting seperation anxiety and it can definitely be worse at night cause they know they're gonna be away from you (sleeping) for much longer than throughout the day. My girl has been the same way plus teething hardcore. It is for sure very exhausting but I know its just getting to sleep that is hard because she is distressed about "being away" for so long :/

@Stephanie thanks!! Thanks make it a *little* better knowing there’s a reason, but still hurts to know I can’t fix it. This makes a lot of sense related to other things I’m experiencing (crying when I leave him with his sitter who he adores and has never had a problem with for the last 5 months, and refusing to go to anyone else at a family wedding where he knew almost everyone.) Do you know if there are any suggestions of how to help them through??

@Beth Honestly, I'm not sure in terms of helping. I think its just a phase they go through and as long as you continue to provide that healthy attachment and show him that you're there, he will come out of the phase more confident 🥰

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