Kevin:

A few possibilities --

- the songs were authorized under two or more different owners
- the songs are in some format other than .mp3 or .aac (maybe they are .wmv 
files, for example)
- the songs were encoded long ago by a faulty encoder that iTunes recognizes 
but the iPad does not
- the media files are scattered throughout his drive(s) and iTunes cannot 
locate them

For several of those problems, your colleague can re-encode his songs (Advanced 
> Create AAC version) or subscribe to iTunes Match (with which I have no 
experience).

See if this archived Apple support article is any help --

<http://support.apple.com/kb/TS1420?viewlocale=en_US&locale=en_US>

Best wishes,
Clint

On May 28, 2012, at 4:16 PM, Kevin Callahan wrote:

> A friend of mine bought his first Apple product: iPad 3rd gen.
> He's a professor.  At the university he has a desktop PC.  He also has a PC 
> laptop which he uses mostly at home or on the road (though he's doing his 
> best to see if his iPad can replace his aging PC laptop - and by and large, 
> the iPad is doing quite well: he pulls student papers remotely from his 
> office PC, edits and annotates them,  sends them back over a VPN connection, 
> uploads them to Dropbox, distributes them to other professors and students 
> etc).
> 
> The problem is with his music library and getting syncing with his iPad.
> 
> His office PC has a bunch of tunes ripped into iTunes from CDs and a sundry 
> of tunes he had purchased from non-iTunes sources.   
> 
> He's discovered that iTunes is not pushing all his tunes to his new iPad when 
> syncing.  
> 
> At first, I figured it was a file format and/or DRM issue.  
> 
> But it turns out, and only for some albums that have been ripped, some of the 
> tunes never make it on to the iPad.
> 
> He can PLAY these non-transferred tunes just fine within iTunes on his 
> Desktop PC, but they just don't get moved to his iPad when syncing.  Repeated 
> syncing didn't help.  Sometimes, he gets an alert saying the files can't be 
> found.
> 
> Frustrated (particularly since I encouraged him to get an iPad and move to 
> the Mac world where things "just work"), he tried syncing his library against 
> his PC laptop.  The same thing happened, but in some instances, a few more 
> tunes (related to full albums) actually got moved over.  
> 
> I asked about his iTunes preferences on his PCs, and specifically, about the 
> following:
> 
> 
> <PastedGraphic-33.png>
> 
> I have mine turned ON.  He has them turned OFF.  
> 
> I assume this means his actual media might be strewn about his Windows file 
> system and causing the sync issue or forcing the alert saying the songs can't 
> be found.  But that doesn't explain (or doesn't explain well) why the iTunes 
> app on his PC *can* play these problematic tunes just fine, ie: it knows 
> where they are, but when syncing, it doesn't know where they are. 
> 
> I'm not sure how to help him.  I would think he should recreate his iTunes 
> library from scratch with the above preferences turned ON.  However, not 
> knowing how his medias is stored on his PC (and having not used a PC in 
> ages), I am hesitant to tell him to delete his iTunes Library and start over 
> fearing he might lose his media if not his mind.
> 
> Thoughts? suggestions?
> Thanks,
> Kevin
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