My almost 8 month old has been waking up 30 minutes every time he falls asleep- naps and bedtime. We are working on sleep training and the initial falling. Asleep is going well but the second wake up is it - any tips or advice?

He’s on a pretty consistent schedule, we do a wind down/bedtime routine.

The second time he wakes up he is not fully awake, we try to let him attempt to self soothe but it almost never works, especially bedtime. Idk if he even is fully awake, his eyes are always closed and he just cries and screams. We try for 15 minutes and do the pick up/settle/put down but he just doesn’t fall asleep again. He isn’t wet and we don’t do night feedings anymore

I just feel so bad for him ☹️☹️