I had the same problem. Ran all the diagnostics and got the message "not detected".
Selected my Classic on the side bar
On the top Horizontal Bar that runs "Summary Music Movies TV Shows Podcasts Audio..."
I clicked on Podcasts: Boom. Podcasts transferred to the old 80 gig classic.
Music? Ditto: that's where you select specific play lists. Haven't succeded there with
getting PodCast Playlists to transfer [the podcasts did] so I've got some additionsl homework.
PS: Been running all this on my newer Classic On my Mac
The above problems were encountered in settingl up on a PC Laptop Running Windoz 7
First time I''ve done a scratch install on an iPod in years. The Mac I don't have to think about.
Wish iTunes Diagnostics asked: "Did you tell iTunes to Sync anything?"
They probably did in the Video.. but hacks like me read all the instructions as a last resort ;-)
I have been sweating for more than a week thinking I would have no music for christmas as my ipod classic would only sync for 10 seconds and no songs would be added to my ipod. To make matters worse, in vain I reformatted my ipod so wiped all my songs and couldn't get them back on. I was blaming apple etc, but ultimately found that when I clicked on the tab that come's up with ' iPod' with the triangle next to it in topish right of the page a new screen came up with an image of my ipod classic. I then clicked on the tab above that said music and found the automatic sync boxes were unticked. This must be a glitch in this update. I hope people find this helpful and is a solution for them. Unfortunately, the iTunes page changing to a very minimalist format does not help navigation. IAnd there I was thinijg finctionality was the focus of these companies.Good luck!