I had the same problem trying to update to version iOS 5. Must have tried 6 times and kept
getting the same messages. Also tried the suggestions in TS3221, NO LUCK!!!
I just don't understand why some tech from Apple does not monitor this forum and try to give
some help. I also wonder if the other people that had problems ever found a solution, if
they did, WHY? didn't they post something.
The first error message I would get stated:
-------------------------------
There are purchased items on the iPod "iPod" that have
not been transferred to your iTunes libary. You should transfer
these items to your iTunes library before updating this iPod. Are
you sure you want to continue?
Continue Cancel
-------------------------------
I would continue. I would then get the message Updating to iOS 5.0.1 will babckup and .....
and it would start backing up. After about 12 minutes of backing up I would get the
following message:
-------------------------------
An error occurred while backing up this iPod
(0xE8000067). Would you like to continue to update
this iPod?
Continuing will result in the loss of all contents on this iPod.
Continue Cancel
-------------------------------
I would of course cancel. I'M SURE YOU WOULD LOOSE EVERTHING
I'll tell you what I found that caused the error on my iPod. Before doing the update I would
Sync, Transfer Purchases, and Back Up, with no problem.
Then I noticed, when I Right Clicked on my iPod name under DEVICES and then click on
"Transfer Purchases" in the Window at the top center of iTunes that it would always tranfer
the same app everytime. It appeared that the app did not get transfered since it would state
that it was tranfering it every time. I therefor deleted the app on my iPod, then tried
another update.
This time I did not get any messages and the update complete.
I think Apple should change the error message about purchased items not being transferred
from "You should transfer" to "You MUST transfer or this update will FAIL".
Hope this information helps.