Hi there, I'm not sure I can offer you much help, but I wanted to pop in and show support b/c my Kyler is 16.5 months and going through similar issues. He started the transition about 13 months and long before he could handle the awake times. Even now it's difficult. We've only been on 1 straight nap for about 2 weeks, and sometimes it's 1/2 hr wakeup crying sometimes 1.5 hrs and still grumpy all day long. Kyler has most always woken before 6:30, it was 6 am since the time change, but in the last few days is now 5-5:30, which like you, is waaayyy too early for one nap. Bedtime is usually 6 but the one time I put him down at 5:30 he woke ealier than 6 at 5:30 for the first time, and since then has been earlier than 6. I too don't know what to do. I don't want him waking till 6:30 or later but he too wakes just talking, not crying, which for him means he's not tired. But in your case 4:30 is way too early, definitely not time to get up. What time is his nap? Kyler's nap is 10:30 right now, but is tired by 9, it's hard to keep him up till then. And usually cries when I lay him down. It's hard to say what to do if he's not crying at 4:30; b/c they say not to go to them if they're not crying. Even if he's up at 4:30 he won't take 2 naps? When my Kyler was that age 2 months ago, he would wake at 5, I would try to get him back to sleep till 6 (never worked just cried) then would be back down at 8-8:30. As long as he's not crying and you don't get him up he gets the idea that it's not time to get up. My only suggestion would be what they told me: see if he'll take a 20-30 min am nap, then try 3-3.5 hrs later for pm nap. My case wasn't that bad, only waking at 5-5:30, so that never worked for me, but that's the only solution I see in your case, b/c he's got to be soooo ot. Can you post your routine?