Apple device changes in MediaMonkey 4.1 may have addressed this. You can test MediaMonkey 4.1 from the MediaMonkey for Windows Beta Testing forum.

I have a similar problem with the latest build - always the same file. I re-ripped the track and renamed it but the problem persists. If I delete the file and synch without it, a different file is chosen for the error message.

Thanks bjbigplayer. I will check that out next time I get the popup message.

[quote="bjbigplayer"]I had this problem with just one file and no matter what I did it always got that error message. I even tried to reconvert the file and the message still showed up, so I deleted it and re-ripped the file. So far so good. My guess is that there is some minor corruption in the audio file that is causing your iPod to do something.[/quote]

Found what it is, you may have an illegal character buried in the filename that cannot be identified by the iOS. Thus your iPod has to modify the filename to function properly.

I had this problem with just one file and no matter what I did it always got that error message. I even tried to reconvert the file and the message still showed up, so I deleted it and re-ripped the file. So far so good. My guess is that there is some minor corruption in the audio file that is causing your iPod to do something.

Is anyone else having this issue?

When I synchronize my iPod Nano, I get a set of popup messages such as the following (even though I have not made any changes to the files on the iPod)

File 'x' was modified in the device. Do you want to copy it over 'y'?
Yes | Yes to All | No | No to All

Even if I pick 'Yes to All' then next time I re-synch the same messages for the same files are shown.

I am running MediaMonkey 4.0.2.1462 on Windows 7. I did not have this issue earlier with v3 of MediaMonkey.

Any insights would be appreciated.
Thanks