My IPOD (classic) plays in only one channel when I plug in the headphones. If I squeeze the top of the IPOD near the input for the headphones, I get sound in both ears, however, if I let it go, sound is in one ear only. Tried various headphones with the same result. Any possible solutions or will I have to get a new one?

If the signal is only coming through the left side, I'd go to radio shack and get an 1/8" male mono to 1/8" stereo female adapter and that'll split the single signal into both earphones. It'll be mono, but at least its playing through both earphones. Much cheaper than buying a new iPod. If the signal is right side, you will need more adapters or something. Let me know which side it is, and we'll see what we can do.

The sound comes only on the left side as you said.

That should work for you then. Again, stereo image will be lost because you'll be listening to the left feed through both ears, but at least it'll sound proper rather than one ear only. And it'll be cheaper too. If for some reason this doesn't work, let me know.

I'm sure you tried a different headset, verify that problem is Ipod and the not headset.
Could be cracked board, cold solder connection, corrosion?

Yes I tried a few different sets. I thought for sure it was the headphones and not the IPOD. I wish it was the headphones although they are Bose and cost almost half of what the IPOD cost.

I just got the same io my iPod touch but the sound came back?

Apples 3.5mm jack sockets are notoriously bad, from iPods to iPhone 3/ 3GS... they all suffer problems, normally with contacts getting dirty and not making proper contact with headphone jacks.
This one's worth a go... lightly spray WD40 or another thin oil onto the jack, and pump it in and out of the socket repeatedly... re-spray, and do it again. This obviously won't resolve a dry joint as mentioned above, but will often do the trick in curing crackly playback, or no speaker sound, but headphone OK, or vice-versa. The other answer is to crack open the player and replace the headphone jack. There are numerous tuition videos on Youtube, and parts are available for pennies on eBay.

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Originally Posted by Sergei Walankov

Apples 3.5mm jack sockets are notoriously bad, from iPods to iPhone 3/ 3GS...they all suffer problems, normally with contacts getting dirty and not making proper contact with headphone jacks.
This one's worth a go...lightly spray WD40 or another thin oil onto the jack, and pump it in and out of the socket repeatedly...re-spray, and do it again. This obviously won't resolve a dry joint as mentioned above, but will often do the trick in curing crackly playback, or no speaker sound, but headphone ok, or vice-versa. The other answer is to crack open the player and replace the headphone jack. There are numerous tuition videos on Youtube, and parts are available for pennies on eBay.

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Definitely give this a try, I was able to fix an old iPod of mine by cleaning out the jack.