The recently-launched iTunes 9 update is causing a variety of problems for iPod classic owners, comments on Apple's support forums suggest. Issues primarily revolve around sync, to the extent that a number of people complain they are unable to to sync media at all. Some Classics may be ejected automatically when connected via USB, while others may cause crashes, or fail to be detected by iTunes, preventing any form of interaction including firmware updates.

Apple has yet to offer a solution for the errors, which appear to affect 80, 120 and 160GB Classics syncing with either Mac or Windows systems. A proposed user remedy involves disconnecting a Classic, resetting it and reconnecting. The tactic may backfire however, as some say they have only been left with an iPod empty of content.