5 Month Napping Schedule

I would try feeding him when he wakes up rather than before the nap and dropping one nap. Watch for his cues that he is sleepy (thousand-mile stare, eye rubbing, yawning) and then lay him down immediately. Stay with him to soothe him if necessary. And stop the rocking, music, movement, etc. Babies at this age become dependent on it to fall asleep & stay asleep. Good luck!

As your son gets older he will nap less and less. Try doing something to occupy him (i.e. play with him). As he gets older he will become more aware of what he is missing and want to be awake more and more. He may even fight naps all together because he doesn't want to miss anything. He will eventually only need one nap per day.

Hate to tell you, but he is ready to cut out a nap! Boo I know...
I have two kids (15 months apart) with my youngest being 6 months old.
BOTH of them around 5-6 months went to 2 naps a day. First nap is at 9am and the 2nd around 1pm.
You just have to face the fact that as they get older they need less sleep during the day and thus requiring more of YOU :) Ahhhh how I miss the days of a sleeping baby all the time.
When he gets around 14-18 months he will again cut out another nap. My oldest got rid of the 9am one and now only does the 1pm one.

You will know the signs when you see it and it sounds like you are seeing them right now. He is clearly telling you that he wants to be awake and he is only falling asleep now because he is comfy in your arms.
Trust me don't fight a battle you can't win. You will go nuts and make him more frustrated with you! Just adjust the naps a bit so 2 are spaced out in the day and enjoy him being more awake and watching him learn things....

My baby does something similar when he is teething. Every time I lay him down he wakes up when his teeth hurt. I am using the teething tablets for this and its really helped.
You can tell if its teething by the drooling, and when I try a pacifier he bites on it. (If you don't use a pacifier try a teething ring or teething toy.) My baby also has a little bump on the bottom where the teeth will eventually come in.
It goes in spurts, some weeks he seems to have pain and others not so much.
Try to keep your routine the same for naps during this time or you may find yourself trapped into a new, longer and more complicated routine that you didn't anticipate. Good luck and I hope this helps.

I'm in the same boat with my daughter - she's almost 5 months.
My first born is 5 now so I don't really remember how he was at this specific age but I do recall as a new mom being completely flustered when I realized that as soon as I figured out his schedule he would change it! Usually about every 6 weeks the first year. ;)
Try a 2 nap day and see how it goes - play with your son so he's tired and then do a bedtime routine for every nap like you would for night time.

Maybe he doesn't need to sleep that much. Cut out a nap and see how he does.

Is he teething? My grandson slept so good for about the first 3 months and then started teething and would only nap for 20 minutes tops a couple times a day. Now that most of his teeth are in he is finally starting to sleep better again.

When my son was this age I finally figured out he started teething and that's why he didn't nap well. Maybe try some teething tablets...HTH!

The only thing I can suggest is to feed when he wakes up rather than before you put him down. I think of it as giving them fuel, you want them to burn it, and tire themselves out. Then when they are hungry, they wake up, and need more.

It is time to cut out one of the naps and you won't have a problem for a while. When he does it again (probably around 14-16 months) take another nap out.

Good luck!