Music randomly disappears during sync with iPhone

When I sync my iPhone with my MacBook Pro, music randomly disappears from my iTunes library. The first time, 100 items "could not be found," then the last time 10 items "could not be found." Songs are still listed in the library, but they will not play and they have an exclamation point next to them. I have everything backed up on an external drive, but it's a pain to have to keep dragging songs back over. This problem began after my most recent OS X update. The items are very random and incude songs purchased from iTunes, songs from CDs I own and "digital book" downloads included with albums I purchased through iTunes. I would very much appreciate any help. I'm afraid to sync music anymore!

Unfortunately, this does not fix my issue. The battery indicator still disappears sometimes (not always) when syncing and I always have the sidebar showing. BTW, this only happens with my 5S not with my wife's 5 or my iPad 3. It used to happen with the 5 that used to be mine until I got the 5S and gave the 5 to my wife. Because of this I think it has something to do with some app I have loaded (but since I have many apps it would be very hard to track down).

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HT2513 one of my caledars disappeared after sync with iphone? where is it? How do I get it back?

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Generally your library will be in your music folder in an iTunes folder, more specifically a library.itl file. If it isn't there then for some reason it has disappeared and can be restored from the backup you make of your computer.

Much of my music in itunes has disappeared since syncing with iphone 4s?

I'm not sure what is going on, but most of my music in itunes seems to have disappeared since syncing with my new iphone4s.
I just noticed this when trying to look for a ringtone to put on my phone. I haven't put any music or anything like that onto my phone yet.
What is going on? Can I get this back? I still have the music on an ipod. most of the music I uploaded from cd to itune.
ty for help.

This is not sounding like an iTunes Match issue - worth trying the iPhone forum and/or the iTunes for Windows/Mac forum.
Usually in synchronisation, pending settings the library will adjust Songs on the device - it is not normal for connect to a device to alter Songs in a library unless to add - for example, addition of Songs purchase on the device.
Would recommend - creating a second library, importing Songs from iPod and making a secure backup - from here you can use this resource to correct your original library, once the issue with your iPhone has been resolved.

Entourage Tasks and iCal "To dos" have disappeared during sync with .Mac

All of my “tasks” (both completed and incomplete) in Entourage and "to dos" iCal have disappeared, apparently during a sync with dot Mac. This problem has happened twice in the past two weeks (the first time I lost all of my Entourage “notes” too, but I haven’t put any back).
The tasks show no problems for a week and then all of a sudden disappear from both Entourage and iCal. My calendar and address book (which I also sync) seem not to be affected. Entourage doesn’t seem to offer a way to sync the calendar without syncing the tasks as well.
Here are my questions:
Why did my tasks disappear?
How do I prevent their disappearance again?
has anyone else experienced this problem?
My Entourage database is fine. I’m running Entourage 11.2.3 (which rencently added a feature "sync services" that allows syncing with .Mac and iCal).

I had the same problem and I got my To Dos to appear when I clicked on the To Dos by Priority column header and checked/unchecked the Hide Items outside Calendar View option. (Doesn't seem to make any difference whether it is checked or unchecked ... it displays all of the items ... at least until restart iCal ... then it is a bit unpredictable.)
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Freeing HD space from iTunes without losing content during Sync with iPhone

Hey, Y'all!
This is probably a common question — but I had some trouble finding a specific answer by a few attempts at searching. So please forgive any redundancy...
I desperately need to free HD capacity on my MacBook Pro, and parts of my iTunes Library would make good candidates. The entire home/Music folder is already backed-up to an ext. HD (more than 1x).
But I'd prefer to NOT lose whatever I delete from my MacBook Pro's HD when I sync with my iPhone 3Gs and my son's iPod Touch. Both devices have plenty of capacity for what they're holding currently.
How do I set up sync parameters to accomplish this using, e.g., the Music and Videos tabs in the iTunes interface with these devices? And when — do I alter these settings "before" doing the removals from my HD? The answers may be obvious, but unfortunately not to me.
Hope I've made sense in stating my questions. I'm using iTunes 8.2.1 (6) if that's a factor in this...
Thanks for your help!

I finally found several errors that may all help you who may have the same problem. While each of these steps may or many not help you, here is what I did to achieve a resolution. I will provide the logic as much as I can.
1. The problem is as above, unchange
Step 1: I made sure that my Mac (late 2008 unibody, running Mac OS X 10.8.2 with all recent updates) was infact working well. I verified and repaired permissions as well as verified and repaired my HD.
Step 2: I went through my iTunes app library and eliminated duplicates as well as apps that 'hung' (apps that would be updated but never leave the update screen- somehow these apps are duplicated- delete one of these to clean up your app update screen.
Step 3: Check for operating mode. You most likely need to run iTunes 11 on Mac OS X Mountain Lion (and possibly Lion) in 64 bit mode. Close iTunes and open your Applications folder. There select iTunes 11 and under the file menu- select Get info. See if your iTunes is running in 32 bit mode*. Uncheck this if 32 bit mode is selected. Close the window and restart Itunes. Try synching with your iPhone or Ipod (touch). This may work.
*Step 4: If you have 32 bit mode checked, think back to if you installed 3rd party plugins. I realized I have a legacy plugin for iToner that forced iTunes 11 to jump back from 32 bit and 64 bit modes. Check your iTunes plugins and either delete or backup/delete plugins.
After doing all this, my iTunes 11 and iPhone 5 started synching again.
I hope this helps. Whenever there are problems in upgrades, check 3rd party plugins! Check that folder to jog your memory!

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My iPhone gets stuck during step 5 of 5 "Waiting for changes to be applied" while syncing with my iTunes Library. I'm using Mac OS 10.6.8, iTunes V. 11.1 and iOS 7

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Version 11.1.5.5 of iTunes was just released today. If you update to that, does that help with the syncing troubles?
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I have a problem with itunes when I sync the saved music and want to sync my iphone 5 ios 7.0.6 no longer passes the music thing is that just stays on "waiting for sync" and not worry please help are more than 400 songs that do not want to hear who are wi

I have a problem with itunes when I sync the saved music and want to sync my iphone 5 ios 7.0.6 no longer passes the music thing is that just stays on "waiting for sync" and not worry please help are more than 400 songs that do not want to hear who are wi

Plawexki wrote:
... do you know if the contacts, photos, messages etc will be wiped?
Yes... Everything will be Wiped and Replaced with what is currently on Your Mac.
SYNCING with iTunes
See here > http://support.apple.com/kb/HT1386
From Here > http://www.apple.com/support/iphone/syncing/
You may find this information of interest...
Have a read here...
https://discussions.apple.com/message/18409815?ac_cid=ha
And See Here...
How to Use Multiple iDevices with One Computer

Outlook Calendar stopped syncing with iPhone Calendar

I deleted a recurrent event on my iPhone and this action appears to have confused the sync capability between my iPhone and MS Outlook Calendar.
Outlook still tries to find the recurrent event on start-up even though it is not shown in Outlook Calendar.
More concerning is that new events and changes in Outlook Calendar are no longer syncing with iPhone Calendar. The time to complete the Calendar sync activity is noticeably longer than any of the other sync actions, which suggests that there is a problem.
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I appreciate that this may be an Outlook issue but are there any other things that I can try to restore the sync capability between the 2 Calendars.
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I'm not sure if this will work for you. It seems every time I research a problem, everyone has a different solution that doesn't work for everyone. (I just spent an hour and a half searching for a solution in various forums.) But this one just worked for me.
I went into iTunes, into the Devices page for my iPhone, then to the Info tab. I unchecked Sync Calendars with Outlook. A pop-up appeared saying, I believe (I didn't write it down) "Do you want to delete previously synced calendars on the iPhone" - or words to that effect. Since I hadn't entered anything directly into the iPhone calendar in a while, I clicked Okay. Then I clicked on Apply (lower right corner of iTunes). The iPhone synced, and all appointments disappeared from the iPhone calendar. I then rechecked Sync Calendars with Outlook, clicked Apply, and the iPhone synced once again - and all my Outlook calendar appointments appeared on the iPhone.
This was, I admit, after having deinstalled all Apple software from my PC and reinstalling it. That didn't work on its own (still couldn't sync calendars), but I don't know for sure whether it had something to do with the success of the de-sync / re-sync.
Good luck. These solutions always seem to be hit-and-miss.

Adressbook sync with iPhone contacts

I got this new iPhone 5 and restored my iPhone-4-contacts on it. Then I made the facebook-sync and now I have all the added data (pics, email-adresses, ...) in my iPhone-contacts.
These added data will not show up in my adress-book on my Mac (Mountain Lion). What did I do wrong?
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Thanks, Gernot

Hi Shady!
I don't think that clearing the sync history is the only cure to this problem. At least it does not help for me. I believe that the problem with contact syncing is not monocausal, hence the cure with the sync history won't heal the manifold of root causes.
My situation is as follows:
What works great when syncing back and forth between the iPhone and the addressbook.app
. *Adding new* contacts or updating contacts +on the iPhone+
. *Editing or updating existing* contacts +on the iPhone+
. *Adding new* contacts +in addressbook.app+
What does not work at all:
. Choosing any existing (created before using or syncing with iPhone) contact and sync it with the iPhone
I sync only a certain group in addressbook.app, not all contacts.
The only way to cure this problem for me so far: Adding a new contact on iPhone or addressbook.app, which is a pain given that all the contact data is already present.
Interesting enough this was not a problem from the beginning. During the first couple weeks or months I could choose any of my "old" contacts and grow that group as I saw fit and everything worked flawlessly...
Very disappointing...

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Can someone who owns an iPhone 4 and has updated to iTunes 9.2.1 explain what this feature is?

Hello, I have the same problem! (iTunes 9.0.1.8 iPhone 3G 3.1.2 (7D11) Windows7 64bit msi EX630 notebook)
My temporally solution is bit anoying but simple!
Everything is closed just iTunes is opened. System performance is set to max level.
So transfer Your music just 1 album at once!
So if You have 4albums to transfer just make it four times. If you transfer single tracks then make it just 8 or 10 songs at once.
I don't know why it works but it works for Me...!
ps: Apple need really fix this! It is annoying!

Avoid installing iTunes 11 if you are a Windows user. Calendars, etc will not sync with iPhone or iPad. Anyone have a fix?

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I'm also seeing weird sync issues since upgrading to iOS 7. The sync issues started when I first upgraded to iOS 7 so I suspect that iOS 7 is to blame and the other system differences aren't an issue (i.e. I also upgraded to Windows 8.1 but it never worked properly when I was on Windows 8). For me, the only way to "sync" all the smart playlists and music is to restore from backup and then the first sync seems to work. However, I haven't tried that recently (I tried it a month back or so and it worked then) because it is ridiculous to have to restore your phone just to sync things! Apple needs to fix the iOS 7 quality issues.

Why can't I add appointments to the calendar anymore? I can add to my iPad and they show up and sync with iPhone but I can't add appointments directly to the iPhone calendar.

Why can't I add appointments to the calendar anymore? I can add to my iPad and they show up and sync with iPhone but I can't add appointments directly to the iPhone calendar. I am on the latest OS version available for iPhone 5s.

Hi,
You cannot manually manage music with match turned on on your iOS device. If you want to manage music manually, you will need to turn off match on your iPhone.
Jim

Music randomly disappears during sync with iPhone

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