Songs seem to copy from iTunes but I can't see it on my iPod?

I am dealing with a strange issue here. I have got the 30GB Black video iPod and I am using the copy of iTunes which comes along with the installation CD. I have preferred to update the music on my iPod manually within the iTunes preferences.
I have a song in a playlist called 'New Hits' which I wanted to transfer to my iPod so I just selected that particular song from within iTunes and dragged the same to the iPod. (Apparently my iPod has a similar named playlist as well). I could see the iPod getting updated and also the song from within iTunes.
What happened later was very strange. I ejected my iPod to listen to the song and I couldn't find it in the playlist!! It's funny that iTunes updated my iPod when I set it to do it automatically. What could be the reason for this behaviour?
I have got the latest iPod software and I verified the same through the installer. Please help me resolve this issue.
Windows XP Windows XP Pro

OK..going by the lukewarm response to my thread, I believe it's not a rare problem after all. Anyway, I have stopped using the manual setting now and reverted back to automatic update from iTunes. This seems to be the only way out to get the songs on my iPod until a relevant solution is found.
CIAO.

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I've just signed up to iTunes Match as I have songs on my iPhone 4 which wont sync with iTunes as they are from CDs but I can't see my music in the cloud now. Anyone had the same problem and have an easy fix?

I've just signed up to iTunes Match as I have songs on my iPhone 4 which wont sync with iTunes as they are from CDs but I can't see my music in the cloud now. Anyone had the same problem and have an easy fix?

What fixed it for me:
On your computer, open iTunes > My iPhone (or whatever name you gave your iPhone) > "Music" page
Uncheck "Sync Music"
Click "Sync" button (bottom right)
Let it run and finish
Uncheck the box for every song, playlist, etc.
Click "Sync" button (bottom right) (This step may be unnecessary, but I did it and got the result I wanted.)
Let it run and finish
Check the boxes for the music you want on your iPhone
Click "Sync" button (bottom right)
Let it run and finish
See if that doesn't work for you. I tried a lot of things that did nothing, but this seems to have fixed it, and quickly.

I rented a film from itunes -but i can't watch it says 'we could not complete your itunes store request. An unknown error occured (-42110)

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I'd try the following document with that one, susanna:
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I created a new playlist on iTunes but I can't see it on my iPhone?

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Hi ik-graphics,
So you synced a new playlist to your iPhone but it isn't available on the phone?
When you synced the playlist to your iPhone with iTunes, did you have the music set to sync the Entire music library or Selected playlist…?
3. Select the Sync checkbox, then select the items you want to sync automatically each time you connect your device.
If you had it set for Selected playlist, please make sure the new one is selected to sync.
Take care,
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just bought an album from itunes but it won't sync to my ipod. i was using a PC but am now using a mac. Is there anything i can do?

iTunes & iPod Hints & Tips
iPod: Frequently Asked Questions

Some songs do not copy from iTunes to iPod

This is very frustrating. I have a 5th Generation 60gig iPod. There are about 20,300 songs in my library, none of them from the iTunes store. All legal, all owned by me and I have the CDs to prove it. When I update the iPod all but about 4 or 5 songs copy over. The frustrating thing is there's no way to find out which songs are not copying over to the iPod, so I can't tell if there's a problem with them or what. AppleCare tells me the only way to find out is to visually compare the list on the iPod with the list in iTunes. I have 20,000 songs here and allegedly one of the most powerful computers you can get and I have to compare two nearly identical lists visually?? Oh, by the way I'm running 10.4.6 and the latest version of iTunes and the latest iPod update. This never happened with my 4th Generation iPod. Any thoughts at all of what to do would certainly be appreciated.
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Are you basing the few that don't get sent to your ipod on the file count? Could there be duplicates? I've noticed that there are some of my movies that don't get sent over but I usually get a warning that they aren't in a compatable format.
There is an option in either file or edit (can't remember exactly where, I'm at work) but you can filter to show all the duplicates. I've noticed that when I drag files over to be copied to my ipod and there are duplicates, it only does one.
After you find the culprits, another thing would be to export the file to your desktop. Delete it from iTunes then reimport it making sure of the file format.
just a thought

10 songs will not copy from iTunes to iPod.

I have been having a problem when syncing my iPod. At the end of the sync, a dialog box appears, saying 'some of the items in the iTunes library, including "song name", were not be copied to the iPod "iPod name" because they could not be found". In total there are 10 songs that I can not copy to my iPod, they were all purchases off Amazon Music, as I had a voucher for the site at that time. When I initially purchased the songs, they were copied to my iPod without a problem, it is only recently when syncing my iPod that this has occured. If anyone could explain to me how to fix this problem, I would be extremely grateful, thank you in advance!

Hi, zoed0775.
Thank you for using Apple Support Communities.
If an exclamation mark next to iTunes media in your library means that either the media is missing from the computer or iTunes is not directed to where the media is located. Here is an article that will help you locate the missing media. I have also included a list of icons in iTunes 11 as it will direct you to the best course of action.
iTunes: Finding lost media and downloads
http://support.apple.com/kb/TS1408
iTunes 11 for Windows: Symbols used in iTunes
http://support.apple.com/kb/PH12306
If the media that is missing has been purchased from the iTunes Store, you can delete the problematic media and download it again free by following the steps below.
Downloading past purchases from the App Store, iBookstore, and iTunes Store
http://support.apple.com/kb/HT2519
Cheers,
Jason H.

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When I bought a new Mac and transferred my library, my purchased songs/movies didn't go with it. Now I can't find them. I thought I remember seeing them with a little cloud icon but I don't even see that anymore.

Since you have purchased a new Mac (which, BTW, is not typed in all capitals) why not buy a Time Capsule <http://www.apple.com/airport-time-capsule/> which is designed specifically to work with OS X and Time Machine?
You don't say what part of your Sony "crashed." If it was not the HDD it is possible to take the computer apart, put the HDD in an external case, then recover the data off of it (including the music) simply drag-n-drop. If it was the HDD that "crashed" that makes it more difficult.
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The songs seemed to not uploaded properly as it won't allow me to click on them. I tried swipe and delete but delete won't appear!

Hopefully Apple is trying to clean up this mess of an opperating system

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Songs seem to copy from iTunes but I can't see it on my iPod?

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