ITunes cannot copy music file to iPhone

I have the same/similar issue. I have a collection of music consisting of CD's ripped to Apple Lossless (ALAC) and MP3 & AAC files of varying bitrates (I am converting all my CD's to ALAC as time allows and I am purchasing CD's to replace all my downloads with). I have done all this on a Windows 10 PC running iTunes 12.5.4.42 (latest version).

Because of the size of the ALAC files I need to have the "convert higher bitrate items to..." option enabled when syncronising with my iOS devices. I have an iPhone 6 and two iPod Classic's of different capacity so I select 256kbps AAC for the iPhone and one iPod and 128kbps AAC for the other iPod.

At some point during the first sync, all the devices come up with "itunes could not copy because the file could not be converted" errors but the tracks that fail are different on each device. My solution is simple. When they sync has finished, disconnect the device, reconnect it, sync it again. Almost every time I repeat the process some of the files that failed to convert on the first sync convert on the second sync, more on the third, etc. After four or five attempts all my files are converted and copied. Not a brilliant solution as iTunes seems to be the problem here but it works and requires minimum extra effort.

The real reason that this happens is because when you have the convert to 128kbps AAC option checked, it syncs the music to your phone at a smaller, more compressed format, that doesn't sound as good, especially for audiophiles. Basically, purchased songs from iTunes are 256kbps, and don't get converted, and protected songs from iTunes (The ones bought in 2007) are 128kbps. It can't convert those protected songs, but I have three songs that aren't protected but give error -3 that they cannot be converted. One I replaced, and the others I have to figure out what to do, but for now you can just redownload it from iCloud.

GDawson wrote:
It happens with only one song.

I'm having the same problem with 15 of my songs as well, some of which are Purchased AAC right from the iTunes store. It only happens when I select "Convert higher bit rate songs to 128kbps AAC"

I don't want to unselect it because I am trying to save space on my iPhone. Hopefully Apple comes out with a fix soon.

I messed around with the settings and found the simplest solution was this... Uncheck the 'convert to 128" option and sync the offending songs. They should work after that, then recheck the "convert to 128" box. It will mean that the songs in questions won't be converted, but the amount of space for a few songs is negligible. Seems the easiest work around for right now.

I tried dunkshot225's suggestion, but when syncing it seems to want to resync all the songs that were previously converted to 128 kbps AAC. It won't merely sync the previously un-synced songs, which is two songs in my case.

In my case, out of 2401 songs I'm putting on my iPhone 4, there are 2 that won't sync. I get the same error reported by GDawson. The two songs that won't sync are in MP3 format, and belong to an album spanning 3 discs with 50 songs; the other 48 convert and sync just fine. Here are the details of one of those songs:

Same issue! There's 4 songs but this one bothers me a lot. It's in Apple Lossless (since iTunes does not take FLAC). Part of a Slayer album directly ripped from CD, then converted to ALAC.

I thought it was the extreme bit rate at first, but seeing that the rest of my 2,400 song 800Kbps+ library syncs fine, I knew it couldn't be the issue.

I'm replacing all of my songs in MP3/4 into Apple Lossless files, so the other 3 songs will be replaced by highest quality CD rips. I hope those songs do not cause trouble like this.

Finally, the option that causes the problem while syncing is the "Convert higher bit rate songs to 128Kbps AAC". I have this enabled, otherwise my 100GB music collection won't fit on my iPhone! So simply turning it off is not an option for me.

The song was encoded on a Windows computer before my switch to Mac, using dbpoweramp.

Has anyone found a fix?

Not a fix but a work around....

Open the track in Quicktime, then go to File / Export. This will convert the track to an m4a file which you can then bring back into iTunes and it will sync ok. You will need to locate the file once imported back into iTunes as the metadata will have been lost.

Hi,

Use this tool to fix the mp3 file, and then it will sync.

MP3 Validator

http://www.gromkov.com/faq/repair/mp3_validator.html

Cheers

mp3val doesn't validate m4a files.