Megan, both of mine were and are short sleepers. Charlee would always be wake for 1hr sleep 1hr or 45mins etc. And Jack is great he will sleep pretty much anywhere anytime, which is a blessing. So he is happy to sleep 15mins or 1hr. And sorry haven't hd much troubles with either of them sleeping in the pram. But out of curiosity, is he still wrapped? If he is maybe he would want to be wrapped in pram also. Or maybe a nice soft blanket or pram liner to lay on might help????. But I just normally push pram back and forth and they nod off normally without to much of a fight. And have you tried covering the pram up with a wrap or something so he can't see anything to stimulate him, this worked really well with Charlee but saying that Jack is the opposite he loves to watch things as he drifts off. Sorry I couldn't be much of help.