iPad: issues with syncing purchases

I need to upgrade from the iOS version 4.3.5 (8L1) I am running on my iPad 1. Before I can do so I need to back up purchases of music, a TV show (Great Expectations) and a movie (The Hobbit) I made on my iPad. This is where my problems begin.

The PC on which I run iTunes is old and slow; I intend to replace it but firstly I need to fix my iPad issues. When I first tried a general ‘sync’ all music not purchased on the iPad was removed from it and ‘Great Expectations’ was transferred into iTunes and off the iPad. On subsequent ‘syncing’ sessions I got a dialog saying that all other 74 purchases would be transferred but every time it starts off with ‘The Hobbit’… and then fails, saying there is inadequate space on my hard drive. This is rubbish because I have (painstakingly) made 46 GB available. For that matter, there is 44 GB available on the iPad. I then get another dialog to say that all content that can be transferred will be … but it never is. It appears ‘greyed out’ in iTunes during initial syncing but then vanishes again with the dialog. I can’t find a way to specifically stop syncing ‘The Hobbit’ (it doesn’t appear under ‘movies’) so that I can get to the music, which I am mostly interested in; perhaps I should just delete it and download again later from the iTunes store?

Furthermore, iTunes refuses to put ‘Great Expectations’ back onto the iPad, saying that this video file type can’t be played on that device. This is also rubbish because I have watched it on the iPad!!

This is driving me crazy and has wasted my entire week… it takes countless hours for this syncing process to work with this old PC and then it fails… repeatedly.
Andrew SmithAsked:
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akahanConnect With a Mentor Commented:
Nasirb, with all respect, I don't think you understand the issue at all.

The original poster is already well on the path to upgrading; his concern is that he doesn't want to lose his media in the process.  Without a backup, if he just "upgraded" from Windows XP to Windows 7, he's liable to lose his media...particularly since it looks like there's some doubt about the integrity of the current file system, since iTunes is reporting insufficient diskspace to copy a movie when he's just deleted many gigabytes.  (I'm wondering, though, whether The Hobbit is more than 4GB and the file system is FAT32, in which case the problem is that the file is larger than the filesystem will accommodate, which is what would lead to the message he's getting.)  With more information, we can make a more specific and constructive suggestion than "upgrade."

The appropriate path will depend on:

- Does he currently have any music/etc. that is on his iPad but is not in his iTunes library on his computer?
- Does he currently have any music/etc. that is in his iTunes library on his computer but not on his iPad?
- Does he currently have any music/etc. that was NOT purchased from the iTunes store and, if so, where is it?  In his iTunes library, on his iPad, or both?
Why are you backing any of this stuff up?  If you purchased it at the iTunes store, you can just download it again.

What operating system are you running on your PC?
What file system are you running on your PC? (FAT32?  NTFS? FAT?)

If you run chkdsk on the PC, what does it tell you?
Andrew SmithAuthor Commented:
Hi akahan,

why am I backing it up? Because I was told the only way to transfer purchase made on the iPad was via an iPad-iTunes conection and NOT from the store and I certainly couldn't find a way of doing it. I have files I purchased from iTunes on my PC and from iTunes on my iPad, plus a lot of music I have copied from CDs and other sources. I just want to get it all in the one place safely!

The problem is 'syncing'... you can never tell which direction it is going to work. Give my a 'copy to' option every time so that I can manage my own files!

I am running Win XP on the PC. I will have to check your other questions when I am home tonight.


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Sorry, I'm not understanding you.  Your postings are inconsistent.

First you say you want to back up "purchases" of music, etc.  Then you seem to be saying that you want to back up music you have copied from CDs and other sources.

I can't tell from your posts where any of this material resides currently, or how you are planning to transfer the material from your existing machine to a new machine you're presumably getting, or already have.

Maybe you could describe your entire situation more thoroughly.  It matters, because unless there's an understanding of what you have, and on what devices it currently resides, there's a good risk that any advice someone might give could end up deleting your music etc.
I understand your issue perfectly as I had the same issues a while ago till I was using windows XP.
As far as my experience goes, Windows XP does have issues with iTunes and syncing. I have not had any issues ever since i upgraded from XP to windows 7.

I guess all the new versions of itunes are made 100% compatible with Windows 7.

I would recommend you to upgrade.
Andrew SmithAuthor Commented:
Dear Akahan & Nasirb,

thank you for the time you have put into considering my problem. Over the weekend I have managed to solve my issues. For the record, I provide a description below:

I was running iTunes version on my (old & slow) DeskTop PC under WinXP; the file system was FAT32. Over the years, I had purchased music from iTunes on this machine but I had also added a lot of music from CDs and records; there are over 1200 songs in my library so I didn’t want to lose these! My iPad 1 was running iOS 4.3.5 (8L1). I had purchased ~ 70 audio tracks, a TV show (‘Great Expectations’) and a movie (‘The Hobbit’) on this device.

What I wanted to do was completely sync the two devices, PC and iPad, so that the same content was on both before I upgraded. I was unable to do this because ‘The Hobbit’ was always the first purchase to be copied from the iPad and this process always failed; the remaining content was not copied.

Over the weekend, the first thing I did was to upgrade iTunes on my PC to version; the Hobbit still refused to transfer, so I deleted it from the iPad. After this, the other purchases transferred across OK and I felt confidant to upgrade the iOS on the iPad to version 5.1.1. This worked fine, but of course all the content: apps, music, video was wiped from the iPad. Next I synced the iPad with iTunes again and most of apps were reinstalled, along with all of the music and (this time) the TV show ‘Great Expectations’; which I can indeed watch on the iPad. It was necessary to reinstall some purchased apps from the iShop and to download ‘The Hobbit’ again. Furthermore, all my Kindle books had to be reloaded.

All up, a fairly painful process. I hope I don’t have to upgrade again before I have replaced my PC!
Andrew SmithAuthor Commented:
Although Akahan did not provide the actual solution he pointed the direction and put a lot of effort into understanding the problem.
Thanks for the update.  Curious - do you know how big a file The Hobbit film is?
I'm just wondering whether the "insufficient space" message was indeed related to it being larger than a FAT32 file system can handle...in which case you're likely to have similar issues when you attempt to sync again.
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