IOS 8 won't sync music with itunes

Checking in with the Community on this issue, I see a lot of old and new names. I think I'm going on close to two months with this issue?

Background -- Windows 7 PC running iTunes 12.0.1.26. Any and all current devices including iPhone 6 and iPad 2 are running iOS 8.1.1.

Issues - since late September, I have not been able to perform a normal iTunes sync without losing some part if not all of my collection of roughly 6000 songs, the vast majority of which were not purchased through iTunes. I get the now famous grayed out circle around red box next to a track, and when I try to play a track, I get a fast forward through every piece of artwork until it hits a track that is still on the device. Usually one of the few that were purchased on iTunes. I have spent countless weeks involving days worth of copying music on and off of devices in order to get them where they need to be, and now I haven't had a problem in close to a month.

Because I don't sync with iTunes anymore.

Here is what I did, here is what I do:

1.) The only way that I found to consistently get the correct data including music onto iOS8 devices is to do it from scratch. Forget backups. Forget anything but setting the device up truly as a new device. Which also means that if it wasn't a brand new blank device, you have to remove music. ALL music. Manually remove all music via "Manage Storage". Manually remove all playlists (make sure you've got all of this backed up somewhere!). Then uncheck sync music in iTunes, and wait hours for it to "remove" music, and count on that same amount of time to add it back when you go to "sync music" again. For me, roundtrip was a DAY for 6000 songs - 12 hours to remove, 12 hours to add back. FYI, I found the process worked a LOT better if you did it in stages - sync calendars, backup, sync contacts, backup, sync everything but media, backup, sync videos first, backup, then finish up with music, backup, settings, etc. Every time I tried to do it all in one first shot sync, bad things happened, mostly music and video related, as in lots if not all missing tracks and flicks.

2.) Taking a step back from all of this, since we know now that it is not an iPhone 6 only issue, or Windows vs. Mac issue, or even an iTunes only issue, it appears to have something to do at the very least with iOS8. It has to be. Moreover, I think it has something to do with iOS8 AND how it manages large amounts of media (music, movies, etc.) that were not purchased on iTunes. That's as close as I can get to the issue, I'm not the one solving it, that's Apple's job, and as much as I've been a big fan of them always and during this fiasco, my patience is definitely running out.

3.) Since the problem continues, I rely upon my iPhone for everything on a daily basis, it's not working right, I can't sync, I need to update music calendar entries and any other number of items on the iPhone on a regular basis, and Apple has not come up with a fix, I have. A temporary fix.

Here is what I do:

1.) Once per week, I go the Apple Store icon on all of my devices and make sure that all applications are up to current version levels. Yes, I have automatic updates turned on, I leave nothing to chance with Apple anymore, I just check and usually I'm up to speed across the board. So I don't have to sync my devices to iTunes to get application updates.

2.) I use an application called GSyncIt to copy calendar data from Outlook to Google Calendar, which I in turn have set up to update on my iPhone. So I don't have to sync my devices to iTunes to get calendar updates. My main iPhone calendar used to be based on Outlook, now it's Google, no big deal. Not sure what the license fee is for GSyncIt but I've used it for years and it works great.

3.) I rediscovered an application suite called Copy Trans. They have two applications of interest - Copy Trans Manager (free) and Copy Trans Contacts ($15 license). The former copies music files without issue directly to Apple devices. The latter copies calendar and contact info directly to Apple devices, again, without issue. It also does bookmarks, notes, messages, etc. So I don't need iTunes to sync calendars, contacts, bookmarks OR MUSIC.

Bottom line - don't sync with iTunes until Apple solves the problem.

Regardless of the cause, if you sync a lot of your own music using iTunes right now, problems will happen, it's just a matter of time. I do appreciate so many people stepping up to share their experiences and absolute assurances that they have found the cure. I have spoken with Apple on more than one occasion, as recently as a few days ago, they are no closer to a resolution than they were two months ago. We need to take care of ourselves on this one, at least for the time being. I am no longer waiting for Apple, I've devised my own fix, it cost me money but it works. Depending on your sense of urgency and wallet, you may choose to do the same.

Forget about syncing lots of your own music to an iOS8 device using iTunes for the foreseeable future. That's the best advice I can give anyone in the Community

PS waiting in the wings for me after THIS issue gets resolved, yet ANOTHER issue (see "iOS 8 Calendar on iPhone showing GMT times for new events"). And the hits just keep on coming! 🙂

Good luck everyone!

Personally, I think we should all send Apple an invoice for the time that we have all wasted in performing / fixing an operation that has worked so well for years, but no longer seems to work terribly well.

I know I wasted many entire days going back and forth to an Apple shop, only to find a way to do it myself...and even then, I no longer have confidence to simply 'plug in and sync' in case a new surprise emerges. I was even cursing myself for getting old thinking I had reached a point where the technology raced ahead of my understanding of it...LOL...

Sigh. VERY disappointed to hear that the 8.1.1 update hasn't changed anything regarding this issue. As soon as I saw the available update on my phone this morning, I couldn't wait to get to work to check this thread.

So, now I hold out hope for whatever the next version of iTunes will be.

MLB32704 ; Could you please post a link to the Copy Trans Manager software you referenced in your post? I did a Google search on it but there are many dubious links that show up. I'll looking for a reliable download location. Thanks!

CopyTrans by Wind Solutions - http://www.copytrans.net/

Has anyone had better luck with iOS update 8.1.1?

I've updated to 8.1.1 on my iPhone 6 and iPad 2, but I am NOT syncing until someone from Apple either tells me that 8.1.1 fixes these specific issues, or someone can point out specific language to that effect in the release notes that came out with 8.1.1. I did not view the release notes, I just did the updates, via WiFi through the "Software Update" option on the devices themselves, and without any physical or WiFi connection to iTunes whatsoever.

Stepping up on the soap box again - with all due respect to Apple, WHY should WE be doing the trouble shooting and beta testing on these issues? These are APPLE'S issues to resolve, on behalf of a very loyal and patient customer base, not the other way around. I've spent way too much time on this already. I'm done. I've got a call scheduled with my assigned Apple contact on these issues for later this week, I do not have high expectations. I'm going to keep using my workarounds and hope that enough people (unfortunately) experience these issues so that Apple devotes more time resources and energy towards actually getting them correctly diagnosed and resolved. Looking forward to 8.X.X. or 9.X.X. or maybe I should be looking at Samsung Galaxies or Windows-based smartphones? This is ridiculous, sorry, I really do love my new iPhone 6, but the extra work that I've been putting in to setup, fix, maintain, workaround, etc. over the last TWO MONTHS, this is time I'd much rather be spending, I don't know, having a life.

Good luck everyone, anyone who actually does an 8.1.1. upgrade then successfully syncs a large amount of their own music over a handful of syncs, I'd love to hear about it. Not saying to do it but I'm sure someone is going to try, just not me this time 🙂

For what it's worth, my own syncing problems seemed to go away a few weeks ago, with the 8.1 update. There were hiccups: some cover art wouldn't sync, and items added to playlists wouldn't sync over to the iPhone until the third or fourth time syncing, but those bugs long predated iOS 8 for me and at this point I consider them "normal" iPhone syncing (mis-)behaviour. Since 8.1, I haven't had the catastrophic issues of music suddenly disappearing, or needing to entirely re-sync my phone. And for the past week or so the syncing has actually been perhaps the fastest and most reliable it's ever been on any of my iPhones. I don't believe I changed anything to cause the sudden improvement a week back.

Of course, your mileage may vary, but if you haven't tried syncing since before 8.1, then you may want to try it again.

I haven't tried 8.1.1 yet, or for that matter Yosemite - the initial release of 8.0 may have turned me into someone who only updates when I absolutely have to.

Could I ask how large your library is?

I have an iphone 5, I used to have close to 1000 songs and deleted a bunch just cause I didn't listen to them or didn't want them taking up space on my phone anymore. For the longest time whenever I went to sync my music (551 songs) itunes wouldn't fully sync. I ended up with about 200 songs on my phone and every time I did sync itunes would always get stuck on "copying files" part of the sync and would just stop abruptly and I just get more annoyed and ******.

WHAT I DID TO SYNC ALL MY MUSIC FINALLY**

First off, any music that may have not been purchased through itunes, I went through and deleted any album artwork that was there which was annoying but oh well.

Then I went to the little preferences thing in the top left corner clicked on 'Library' and then 'get album artwork'.

Next, I re-downloaded itunes cause I knew it wasn't the correct up-to-date version.

I made sure my phone was fully updated. As of today or yesterday- I can't remember- iOS 8.1.1 came out. So make sure you have that.

Next, I changed the settings in itunes on my computer. When you plug in your phone go to the music tab and unclick the sync music button, press apply, and then click the sync music button again, and then apply once again. **I've read somewhere that just clicking that has worked for some people just by itself**

After that I went to the summary tab while my phone was still plugged in, scrolled down, and unclicked the "automatically sync music when iphone is connected" AND the 'manually manage music and videos button' then I clicked the 'sync with this phone over wifi' button.

I exited out of all the apps on my phone, prepared myself for disappointment once again, and pressed the sync button.

Somehow magically it worked and I wanted to cry and I did a little fist bump cause I've only had about 200 songs on my phone for about a month now and I work at a job where I'm constantly listening to music. So my day is a lot better as of right now. Immediately after I backed my phone up just incase if there are more problems later on.

I seriously hope someone reads this and sees what I did and I hope it is the answer to all of your problems! I'm going to try updating the music on my ipad mini and see if it still works and if not then I'll continue trying to find a solution and update this post!!!

Good luck to you all!

My library size: music 17,000 items or so, 112GB; audiobooks (most of which started their lives as podcasts) 15,000 items, 140GB; iTunes U another 500 or so items/32GB. So total around 32,000 items/300GB.

For what it's worth, way back I went through the steps to remove any non-audio files from my music library, and the nth attempted sync suddenly worked, coincidentally or not. Then I never synced again until iOS 8.1 came out. Who knows which if either approach solved (sort of) the problem; note that the only non-audio files were the liner note PDFs included with iTunes store purchases, so if that was indeed the cause of the problem, it's a serious screw-up on Apple's part.

I also did tons of the other check/uncheck/manage whatever options people have suggested, but none of them "stuck" as a solution for me. But the iTunes/iPhone sync problems go back a long long time, and I'm not sure if the process has ever "just worked" for me; the iOS 8.0 release just took what had always been a problem and made it, in my case, catastrophic. With iOS 8.1 it's now working quite well (touch wood!).

Same problem here. Very disappointing Apple. I watched 9,000 songs sync to the phone only to find 100ish available on the phone and about 45GB worth of "other" showing in the phone's usage meter. I'm gonna try disabling "convert higher bit rate."

The same situation has happened to me with my music library on my iPhone 5 since the iOS 8 upgrade--and with each subsequent 'fix.' What's really appalling is that Apple doesn't have an answer or fix posted for this yet!!

Neither the content or the tone of this post helped me. This poster assumes we are are all lazy, stupid, or illiterate (sound familiar?). I have read all the posts and tried all the fixes. I confident I've forgotten more tech than this guy knows. I can tell you for a fact that nothing works.

I didn't do something different that caused the problem. The problem does reside with Apple and this update. Everything worked fine before the release of iOS 8. The folks complaining here aren't whiners, they are customers who deserve to get the product and service they have paid dearly for.

Why is it our job to figure out how to fix this problem in the first place? Everything worked fine until iOS 8 showed up. We didn't break this. With regard to the friendly recommendation that we should just delete some files that don't belong in the iTunes directory, which ones would those be exactly? Thanks for the specifics and heavy dose of condescension pal. Also, I don't own a Mac so this advice is probably useless anyway. I'm also canceling my order for the iPhone 6+ if this problem isn't fixed real soon.

Thanks for wasting my time and please enjoy your new position as chief Apple smoke screen generator..

I too have a similar problem -- I was trying to get my holiday playlists from iTunes added to my iPhone (6). No go.

I realize that as new versions of iTunes, IOS and hardware evolve that testing all possible conditions of changes becomes increasingly difficult, but it seems like synching music between iTunes and a phone would be one of the more basic tests before rolling out updates. I am confident they will get this issue corrected eventually, although I'm not holding my breath that I'll get my holiday music on my phone for this season--although that isn't a huge deal in the great scheme of things. But to me Apple is no longer the company it used to be in terms of customer support. Just my 2 cents.

My sync problem has been going on since I updated to IOS 8. I have had two telephone help calls and one Genius Bar visit. I am no further forward.

MY iPhone and iPad will randomly fill to capacity with OTHER files requiring a complete reboot. I have disabled iCloud drive and tried reorganising and deleting files from my iTunes library. All of my devices worked almost perfectly prior to this upgrade. I now dread syncing either of my devices to see what latest iTunes problem is now present.

I Have one simple question which no one at Apple has answered. When iTunes finds a file it doesn't like or will not sync why does it not flag it up with the reason for the problem. iTunes has done this for many years with incompatible files and missing album art work. If iTunes could only tell us why it is continually waiting for sync to start or give us a reason for our iOS device suddenly filling to capacity with OTHER files at least we would be able to do our own diagnosis and repairs. Apple need to sort out this issue soon. I'm losing patience and faith in Apple products. So no iPhone 6 upgrade for me till this gets properly sorted.