Can't synch to itunes. Error -39

Hi RaddMann:

Have you tried the new iTunes v. 10.3.1 (released June 9, 2011)?

According to the changelog on the FileHippo site here, the new v. 10.3.1 fixes an iOS device syncing bug that occurred for some users using iTunes 1.3.0 (released 2 days earlier on June 7th).

Dave Taylor posted a similar problem with his iPad here that you may be interested in following.

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MS Windows Vista Home Premium 32-bit SP2

iTunes v. 10.3.0.54 / iPod nano 2nd gen software v. 1.1.3

HP Pavilion dv6835ca, Intel Core2Duo CPU T5550 @ 1.83 GHz, 3.0 GB RAM, NVIDIA GeForce 8400 GS

From other threads, it looks like this is related to photo syncing.

Take a look at this post ->

jdsweet: I had this problem (though limited to the photo-syncing portion of the sync cycle) recently with an iPhone, rather than an iPod Video. I fixed it by going into iTunes, selecting the iPhone, selecting the Photos tab, unchecking "Sync photos from [iPhoto]", accepting its request to delete all photos from the phone (figured that my clear out any issues). That took at most a few seconds (w/ 2200+ photos on it).

Then, still on the Photos tab, I re-checked "Sync photos from [iPhoto]". After that I synced (don't remember if I initiated that manually with the Sync button, or if iTunes started it automatically). Took a few minutes to copy over all those pictures, but then it was fine.

Don't know cause for sure. Though around same time I'd undocked just after importing some photos while the "Delete Originals?" prompt was on the screen, i.e. may have corrupted the finishing stage of a photo sync.

from https://discussions.apple.com/thread/1327353?answerId=6863979022#6863979022

Try unchecking photos in iTunes and checking it again, to remove photos from the iPhone and then sync them back.

WTH.