I have music that is playing within the iTunes program, but not on my iPod. How can I fix this?

Skipping songs
The iPod seems to fail to play all of the occasional track that iTunes, and indeed other PMPs, are happy to play. There is probably some minor technical error in the internal structure of the file which is normally ignored by other playback software but causes the Classic to bail out.
If you use Windows you may like to try scanning the files with MP3Validator which can find & fix some internal MP3 errors.
Some users have also suggested that completely removing all id3 tags and then replacing the information can be a solution. This can be achieved in iTunes by selecting an affected track, right/control clicking and using the option Convert id3 tags> None. Since some files may mistakenly have more than one tag you may need to repeat this action. Once you have confirmed that no tag is present you can replace the tag information using Convert id3 tags > V2.3 (I believe it is recommended to avoid using V2.4).
Personally I have found files for which these solutions don't work. In this case the workaround is either to re-rip the tracks or get iTunes to re-encode the file, e.g.convert AAC to MP3 or vice versa and sync the newly encoded file to the iPod instead. Because transcoding will cause a loss of fidelity you should keep your original file so that if a future iPod firmware resolves this issue you can put your original files back onto the iPod.
tt2

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Welcome to Apple Discussions!
1) If the iTunes preference window is open when you connect your iPod, the iPod will not be recognized by iTunes.
Also, iPods can work with many iTunes libraries, so that is not the problem here.
Is all the software on your computer up to date?
iTunes
iPod Updater
Updating iPod's Software
Does the iPod show up in My Computer when connected to your computer? Does it say Do Not Disconnect?
Try the steps listed here...
iPod shows up in Windows but not in iTunes
If you are going to use your iPod with multiple iTunes libraries (home and school)...
Using iPod with multiple computers
2) What part aren't you understanding. Here are a couple of free programs you can use to convert videos...
MPEG Streamclip
Videora iPod Converter
The programs should come with documentation and instructions to convert videos.
3) You can go to file-->add file to library, file-->add folder to library, or have iTunes open and drag the files into the iTunes library while viewing the library.. You can also import from CDs.
iTunes needs to be adding the songs to the iPod. You cannot just add the song files to the iPod.
btabz

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