Sync All Photos from Aperture: Unknown Error (-50)

I am having the same problem, but I didn't install Lion yet. I have iTunes 1.4 (80) though, I suspect it started happening after updating to it. (I am still running Snow Leopard because one of the 3rd party audio drivers I need for my work has to be updated for Lion first).

I am syncing to my iPhone 4 to my Aperture 3 library. I haven't had this issue before. It syncs everything else but when iTunes goes from "Analyzing Photos" to "Optimizing Photos" in the sync process it reports that it is unable to sync because of an "unknown error (-50)"

To resolve the problem, I tried the following:

• I repaired my Aperture library database (using Option+Command when launching Aperture 3).
• I deleted the "iPod Photo Cache" folder inside my Aperture library. It had to resync all my photos again, this time it worked when re-syncing the entire library, but the next sync it had the same error again.
• Updated my iOS to the latest version.
• Repaired Disk Permissions on my Mac.
• I changed USB cables and ports (using only ports directly on my Mac Pro).
• Tried syncing with only iTunes running.

Doing all the above made no difference, I am still getting the error message and it won't sync new photos back to my iPhone 4 now. It is very frustrating.

This Worked for me:

http://support.apple.com/kb/TS1314

Just go to the aperture file and delete the ipod photo cache..

Good Luck

Thanks, though I have done that (deleting the "iPod Photo Cache" folder within Aperture) and indeed it works during the process of re-syncing all your photos back to your device, but the very never next regular sync results in the same error code appearing and it fails to sync new images to the device.

This error has been annoying me for the better part of 3 months now. I first noticed it when trying to update photos on my iPad after a while.

Troubleshooting for suggests that it is specifically to do with selecting faces as part of the photo sync. Unselected, any albums or selected albums sync just fine, but the moment I select faces it all goes to crap.

Delete the iPod photo cache and regenerated and it worked fine for a period of time, but then you happen to plug in one day and you get Error -50 again.

I even tried deleting all my keyword metadata, thinking I might have had an illegal character that was causing it to barf. no luck there either. At least next time I am unwell I have a task to sit down and re-add all the keywords.

Usually I get something like this in my console at the time of the error -50

2/08/11 6:58:50.296 PM com.apple.usbmuxd: MuxSendToClient send failed for 0x2-b1350cfe08043000a29099618cfa72141e8b4039@0xfd100000:53578->0x10181c110-iTun es/com.apple.iTunes:11521: 32 - Broken pipe

Here's hoping a more permanent fix appears soon.

Hey guys,

this worked for me!! just removed the ipod photo cache from the package contents.

follow the link below!!

http://support.apple.com/kb/TS1314

Hope it works for you.

Hi Breathnobbah,

I think you'll find that if you read our posts, we have all done this, and it has worked for a short period of time afterwards but the problem is quick to manifest itself again.

It's definitely an iTunes or Sync Bug.

I too am suddenly having this error. It occurs during step 5 of 5 during syncing while "Optimizing Photos".

Two days ago I added a significant number of pictures to Aperture, not sure if that is related or not.

Running Snow Leopard 10.6.8, iTunes 10.4 (80), Aperture 3.1.3, iPad2 64GB/ATT 3G, iOS v4.3.5 (8L1)

8GB of free space available on the iPad2.

Adding me to the list. Same problem happing on iPhone 4 and iPad. Following the Apple support article (http://support.apple.com/kb/TS1314) can only fix the problem for one time. The same error will re-occur at the next sync.

I have finally resolved by the problem. Here is what I did.

1. Changed the photo to select albums and projects, and check all albums and projects. --> Error -50
2. Randomly unselected some Smart Albums --> Sync Successful
3. Added Smart Albums back one by one, and found that Photos in Last Week was creating the Error -50. Removed that Smart Album. --> Sync Successfull
4. Chose to sync all photos again --> Error -50
5. Noticed some faces were shown as duplicted. Some are duplicated up to 5 times. Also noticed some unknown names in the face list. All of the duplicated and unknown faces contained only 1 photo and all of those didn't shown up in Aperture.
6. Removed duplicated names: Assign an unrecognized face in Aperture to duplicated faces by typing in the name. As I started typing the name, a list of duplicated entries appeared. I assigned a unrecognized face to each duplicated entry so it would show up in Faces in Aperture. Removed or merged the duplicated faces (Cmd-Delete) in Faces view.
7. Removed unknown names: Used similar steps above
8. Sync all photos succeeded!

I believe it's the problem with the Faces that caused the error. If you try this steps, I would recommend to fix the faces first, instead of starting with the ablums. I believe the problem with faces was what caused the problem.

Unfortunately I haven't had much luck doing the same... I had unselected all faces and I still get the error code. I have tried certain projects... some would sync, others would not. Even the set that I had successfully synced, the next time I tried to sync again, I got that bloody -50 error code.

All had been working fine until the iTunes upgrade to 10.4 (80) and the problem presists with iTunes 10.4.1 (10) which I have now.

I really wish Apple would fix it because I haven't been able to sync photos to my iOS devices for months now.

It definitely has something to do with Smart Albums for me... Clearing duplicate faces didn't work for me, but if I don't select any Smart Albums I can sync everytime just fine. With Smart Albums I get the -50 error until I clear the iPod photo cache, then it works for a short while and begins again.

Frustrating!!

100% correct. I just played with it some more and deleted several Faces from Aperture that may have originated with Facebook tags. Now i sync just fine again, including my smart albums.