So I have an old iPod Photo (color) 60GB iPod that’s been working great for a long time now (since July 2005!) that I use for my office music while I work. I’ve just now finally run out of space on it and so I thought I’d use iTunes’ “Convert higher bit rate songs to…” feature to cram my growing collection onto the existing iPod. I’m on an iMac running 10.7.5 and I was connecting via a USB cable.
Nice idea but it always fails after few hundred songs when I try to sync with this setting turned on. Grrrr.
Tried turning off “Enable disk use” because there was always an error about the disk being unmounted improperly when it fails. No dice.
Finally thought that maybe it was a USB issue and so tried connecting it via Firewire (which this older iPod Photo can do) and Bingo! It seems to be working (4860 songs of 7839 copied so far without a problem).
Thought I’d write this down here so others could find it. I should file a radar but I’m having trouble imaging Apple caring about this old device… Could be an underlying USB issue though…? Anyway.