4.5 m/o waking soon after falling asleep?

We sleep trained my 4.5 month old using CIO but I’m a little stumped with where we are now. We’ve gotten to a point where he does one of two things:
  • Falls asleep without crying, but wakes up a short while later (e.g., 15 mins) and cries for 20 mins before falling asleep again.
  • Cries for anywhere between 5-30 mins and then falls asleep.
In both scenarios he later wakes up about 3.5 hours after his pre-bedtime feed. We’re still going by wake windows so bedtime is variable, but hovers somewhere in the 7-8 pm zone.

The first scenario where he falls asleep on his own but then wakes up hysterically crying has me scratching my head. Any ideas? Thank you!!
 
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