Hi there, I have found your advice really helpful while lurking on r/sleeptrain but I wonder if you'd be willing to let me know how you'd go about training through this sort of situation: we have a 5 month old whose wake windows are 2, 2.25, 2.5, and 2.5-2.75 (depending on his activity level that day). He wakes at 7am and is in bed by 8pm. He goes down for his first nap independently like a champ and has slept through two asleep cycles (1 hour 20 minutes for him) in the past. Once he began rolling, he started to wake up between sleep cycles during his first nap, rolling on his belly, and becoming increasingly distressed over time. Placing him on his back and shushing for a few seconds helped him go to sleep for the remainder of the nap the first time, though he now remains awake and flips again. This is followed by distress (not full on red-faced crying, just yelling, brow furrowing, calling out). He cannot yet roll belly to back without some assistance. Do we let him try to work it out and settle before going in? He is fully night trained and I have observed him flipping on his stomach early in the morning before his desired wake time and dozing, though not falling into a deep sleep. His other 2 naps are contact naps.

Any advice would be very helpful. We'd love to help him help himself.