2pm is the latest I let him sleep. So usually I’m trying to get him to start waking up around 1-1:30. It’s a little different everyday. We start bedtime at around 9pm he just does not go to sleep until around 11:30pm because he fights bedtime so hard
What happens if you wake him up earlier in the day? My daughter wakes up between 6:00-6:30am, naps 12:30-2:30, and is ready to go to sleep by 8pm. We have a 1 hour bedtime routine and I think using a dim lamp during that time helps her body naturally get sleepy. I also agree with the suggestion that you are missing the 'window' and think it might sound crazy but you could try to put him to bed super early one night, like 7:30 and see what happens.
So your son is awake from 2:30-11:30p (9hrs)? I had to cut my son’s naps to 1h30m-1h45 mins max, as 2 hrs was making bedtime late. He sleeps from 8/8:15p-9a then naps 1:30-3:15p. He’s also EXTREMELY active. What time do you start bedtime for your son? Maybe it’s a little late and should be a little earlier? Maybe he’s past his ‘window’ at night, and therefore ends up staying awake even later? 🤷♀️ ideas …