iPhone 4 Syncing Problems?

I was syncing music by playlist, artist and genre in order to get in under the space limit... I unchecked all genius playlists first, but still had the failure. They I unchecked all smart and normal playlists as well, but still had the failure. Then I unchecked all artists the began with a "B" (shot in the dark), and this appeared to be working until it got to Dwight Yoakam and failed again. I unchecked him and now it fails on Kenny Loggins...

Now I'm thinking this is an Apple plot to embarrass me by exposing my taste in music, by only failing on weird soft rock... Why it doesn't fail on a Muse song, I don't know... LOL!

I can't find a common characteristic between these songs that are tripping up iTunes... They are different lengths, different bit rates, they have deferent meta-data. I'm at a loss.

But it clearly is something about these particular files, because when I remove them, the programs continues on to the next as if nothing went wrong. Then, after excluding all the trouble files (that worked without issue until now) and completing the sync, I add them back in and they still cause a failure. I can rename and re-encode through itunes, but those files will not work.

I believe I have found the cause of the problem... Unlike previous iterations, either itunes or the iphone 4 is imposing a character limit.... Try shortening the file name....

I'm sure of it now... The character limit is 107 for the file name... I don't know if this a new limit or not. My ipod worked with these files at their original length...

If iTunes is not syncing, make sure the file name is less than 108 characters (107 or less)

Did this work for you as well? Anyone from Apple have a comment?

I am having very similar problems to the ones described here. I am using Windows Vista and syncing my iPhone 4 just doesn't happen, brings iTunes to a complete standstill.
I took my laptop along to my local Apple Store to see if they could help. After going through some standard things, and consulting technical help online, the advice was that the issue is with Vista. Due to the numerous processes running in the background, iTunes finds it difficult to cope with syncing with the iPhone 4.
The suggestion was that either reinstalling Vista or upgrading to Windows 7 may help.
I believe Apple are aware of this issue so may be able to fix it with a software update, but not sure if this is planned.
Any further help would be appreciated. In the meantime my iPhone will only be being half used, which is a shame.

Mine does the same thing. Just endless syncing iphone in itunes and on phone. It seems like it is syncing. However the one photo album I want doesn't get put on. It'll transfer music fine. Then just goes back to syncing. I have all syncing options unchecked mainly and haven't found any combination to work. It worked fine since i've had it (launch) but now just recently having troubles. Under 4.0 and 4.0.1

Latest updates on everything.

Well a restart fixed the endless sync. However. It said it sync'd my photos (8) but opening the photo app, the album is not there. W TF. So I think to myself, wait a minute. Bring up the "backgrounder bar" kill the photo app, then reopen, sure enough there it is. Did Apple even test this stuff?

Message was edited by: csmitty

I am using Windows 7 Home 64 bit and just downloaded the "64" bit version again. I uninstalled iTunes and I am still having a VERY SLOW syncing problem.

I have given the process a high priority and I had rebooted my PC and my iPhone. Still the same issue. I am able to get one maybe two songs on my iPhone before iTunes starts to crawl. I just don't understand this. It has taken hours and my iPhone is still not 100% complete.

I have a similar experience to what everyone else is saying.

Except my iPhone 4 is three days old, and this problem occured on day 1

I got a few apps, and some music, my contacts etc onto my phone fine, then it broke. I went over websites gallore, but my computer crashes when I attempt to sync anything.

I have removed all traces of apple from my computer and re-installed 64bit again, time will tell if it works.

I managed to sync about three apps up before it crashed and I had to force reset my computer. Oh well.