I have been having the exact same issue in syncing my iPad to my iMac since the most recent iTunes update last Friday. I have tried everything under the sun that has been suggested to correct the issue, but keep getting the same error message every time ("The ipad cannot be synced, An unknown error has occurred (-50)"). I've pretty much come to the conclusion that the issue is with the iTunes update itself, and it's something that Apple needs to fix, post-haste. At the very least, my friend, we can take solace in knowing that we aren't alone in our frustration.
I've got same issue on iPad mini and iPhone 5s.
Went to apple Genius Bar last Monday who could not resolve the problem and suggested I wipe the Hdd and reinstall mavericks etc.
Did that yesterday and still unable to sync - still error -50.
They thought it may be sophos preventing access, but I've only got basic osx and iPhoto on the Hdd and still not joy. I had 19k photos sync happily before I updated to mavericks, first sync wiped the lot and I've not been able to get any images onto any device.
I have tried everything suggested - my iphone 5s, iphone 4s & ipad 3 all have the same error when i try to sync photos - if i leave photos off sync they then work ok.
I have found one thing that has worked. I created another iphoto library and at present have just put 1000 photos in from 2 of my albums. They all then synced perfectly including the photos in the 2nd library. It then obviously seems to be caused by the iphoto library not working with itunes. I will continue to add more of my albums to the new library and see if any problem arises.
My one question would be if and when i have put all my albums & photos into the new library will I then be able to delete the old library without losing any photos from my macbook?
If anybody knows the answer please let me know
Taking a leaf from l4xam, I resorted to renaming my original iPhoto library, creating a new library from scratch, and importing the original and modified folders from the original ( show package contents on original library via right click on it in finder )
For some reason 82 JPG photos some from 2009 are ' not compatible ' any more and where I had 19.5K images I now ( obviously ) have more (28K).
The major issue now is I've lost the original events, now left with mostly date time named events, I've lost the faces too and places too!
Sledge hammer to crack a nut to resolve an issue I did not cause ( except by upgrading to mavericks that is )
I'm considering keeping multiple secure copies of the original library ( over 18 years worth of photos and scanned images and negatives ) and starting a new image library for 2014 and beyond.
If apple can sort out the issue, I may then consider merging old and new libraries at a later date.
having the same kind of problem here: could not sync any 1,2,3, most recent events using iPhoto then after I have read your posts I have decided to export to a regular folder on my desktop, and all the events I am interested to have synced in my iOS devices are synced with no problem-all happens swiftly.
Lately happens a lot, Apple is abit careless will they fix it?
I start having serious doubts
finally found time time to rebuild the photo library from scratch.
it took 2 Hdd or sd cards formatted to osx journaled and large enough to hold the library a few times over ( e.g 2 discs with over 128 Gib space on each )
I copied the iPhoto library to one backup disk and locked it away safely just in case!
I did not have enough space on the Mac to build a new copy upon it so i moved the iPhoto library lock stock and barrel to a second external Hdd
I then opened it in iphoto and selected all the events and exported them to the same external Hdd using the export function, selecting the current version of the file, in the original format and the event name as the folder
it did not export 41 movies ( mov files ) and i have no idea why they are no longer compatible, but it listed them by name
i then created a new iPhoto library on the Mac and imported all the events I exported
it messed up a few dates etc but I can correct those in iPhoto with the menu options
Plugged in both the iPad mini and iPhone and it has synced with no issues
I've lost the faces etc so I'm going to redo those over the next 12 months
20k images in 500+ events and shrunk the library from 75Gib down to 45 Gib as i no longer have both original and modified images.
After trying everything to sync Photos, including a Complete OS X Restore, nothing worked.
I found the solution to Sync Photos from OS X Mavericks 9.3 using iTunes 11.4 is to reinstall Mavericks.
Fortunately I had a copy of the "Install OS X Mavericks.app" in Applications, this overwrites OS X and gets rid of the iTunes 12.01 Pox and the Yosemite Pox, that completely infects OS X.
I also have a copy of the Mountain Lion.app in applications.
Best to be prepared for any Future Apple balls ups!
Regards to all,