Hi there, just to throw a spanner in the works could you try giving his nap earlier? Then he would have a longer stretch til bt, and be more tired. Might work particularly if he's looking tired all morning like you said. I just wonder if he's really ot and it's perpetuating the cycle. I could of course be completely wrong as I know children of this age can stop napping. My dd is about 2 months older than your ds and she finds it hard to sleep if I leave it til 130pm to put her down for her nap, and she wakes later than your ds. They are of course all different, so please ignore me if needed as you know your lo best!