Won't Sync Automatically

My iPhone no longer syncs automatically when connected to my mac. The iPhone is recognized by iTunes, but will not sync unless I click the Sync button. I have the 'automatically sync when phone is connected' option checked. I've tried turning this off, applying and re-enabling, but no change. This has worked in the past, I only noticed it was not syncing in the last couple days. I'm not sure if the 1.1.1 firmware update is related.
Any ideas?
Thanks

Oh, wow. I was having the same issue and was starting to worry that Leopard had somehow hosed my iPhone. Some sort of cue that that setting is toggled might be in order, say, like greying out the "Automatically Sync when this iPhone is connected" checkbox.

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    Hello.
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    Hey, I'm probably too late and you may have already solved it but here's a solution. In iTunes go to Edit then preferences and then click on reset dialog warnings. What happens is when you first sync your ipod, you receive a message saying something like transfer?and you've probably selected "Do not show this message again". I don't really know why but iTunes assumes that the apps on your iPod are already on your computer and therefore need no transferring.
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  • I did allllll that is listed below, but when I get to sync iPad, it won't sync, what do I do? Preparation Before you connect any device to a new library go to the Devices tab

    THis is what I did, but when I get to sync, it won't sync.....what do I doLynnLynn
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    For the future you should backup your library to a separate hard drive or network share as restoring a backup is much easier than the process above. The user tip Backup your iTunes for Windows library with SyncToy gives a suggested way of doing this effectively for Windows users. Mac owners can make use of Time Machine, or useCarbon Copy Cloner which does a similar job to SyncToy.

    This is the ipod touch forum.
    Try posting in the ipod nano forum.

  • Ever since the new update, my Ipod won't sync. Starts to sync but then goes back to connected eject before disconnecting. Still won't transfer songs even after being restored. Restored fine. But now I've got nothing on it. Please god help!

    For awhile, since the newest update, I'd noticed when charging the ipod (classic) that it stopped going to the charging screen and would stay on the  Connected: Eject before disconnecting' screen. But, y'know, didn't matter to me, it still charged... until today when I tried to add music. Tried it many times, reset it... STILL wouldn't transfer songs... It would 'say' it was syncing, but then suddenly stop and stay on the same Connect: please eject before disconnecting' page. I did a couple of times get a message about scanning it but, after restoring that never popped up again...
    So, I do a system restore on it and ofcourse THAT works, but it STILL won't sync! So, now I've got an ipod with no music that won't sync and because it's all gone on there, I'm not sure how to back up my stuff (should I need to re-install iTunes... Though I doubt it'd work...)... So, yeah, I tried a different cable too, still no luck...
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    I think the problem is that the iPod got set to Manually manage music and videos.  It needs to be set up for automatic syncing again.  Just unchecking that Manually manage music and videos setting does not do it.
    In iTunes 12, select the iPod in iTunes (using the device button), so that you see the iPod's "management" screen.  In the sidebar (along left side of screen), there are two headings (Settings and On My Device).  Under Settings, click on Music.  To the right, you see the iPod's Music screen, where you tell iTunes how to sync songs to the iPod.
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  • IPod won't sync to iTunes - Please help! Tried everything

    My iPod won't sync to iTunes. I pug it into the computer, the computer recognizes the device. It automatically opens iTunes once it's plugged in. I was able to system restore via iTunes when the iPod was connected and it wiped the iPod. But when I hit sync it doesn't sync. When I hit the sync button for about 5 seconds the wheel will rotate on the iPod screen and say "syncing" but nothing happens on the iTunes side, (you know normally when your iPod is syncing at the top of the iTunes window it will say "syncing" and you can see the process happening as it quickly runs through the new music it is uploading, this doesn't happen.) I tried restarting the iPod and the computer, system reset, I checked in the control panel to make sure the apple device was started, (which it was,) and even bought a new sync cord to be sure. Nothing. Any ideas?

    I was running into the same/similar problem. Is this a new computer but old ipod?  In other words, does your ipod contain music from a previous pc?  If so, that might be the problem.  I bought a new pc and adequately transferred my music from old pc to new pc.  My itunes library on new pc was where I wanted it to be.  But when I tried to sync my ipod later, it wouldn't sync.  Would stop at first step like yours was doing. 
    If this is the case with you, open your ipod information on itunes.  It will automatically be on "Summary".  Click on "Music".  You will see a box labeled "Sync Music".  Click on that box.  Then you have the option of checking "Entire Music Library" or "Selected playlists.....".  I chose entire library.  When you sync, it will warn you that you will be erasing contents of ipod and replacing with contents of this itunes library.  Like I said, my library was good.  So I chose ok.  It synced fine after that.

  • IPod Won't Sync After Moving Music to New Computer

    With the help of someone here, I moved my iTunes Library from my old computer to my new one. It didn't work exactly like it was supposed to. All of my music is on my new computer and in my iTunes library, but my playlists, counts etc. are gone. Whatever - I'll deal. Now, though, my iPod won't sync with my new computer (which I did authorized). The "Do Not Disconnect" sign never goes away after I connect my iPod. Thoughts?

    *I'm afraid to plug in my iPod in fear of it erasing my playlists...*
    If your iPod is set to update automatically you need to take care connecting to a different iTunes. You'll get a message that it is linked to a different library and asking if you want to link to this one and replace all your songs etc, press "Cancel". Pressing "Erase and Sync" will irretrievably remove all the songs from your iPod. When your iPod appears in the iTunes source list change the update setting to manual, that will let you use our iPod without the risk of accidentally erasing it. Check the "manually manage music and videos" box in Summary then press the Apply button: Managing content manually on iPod
    You can also use a keyboard command to prevent your iPod auto-syncing with iTunes. While connecting the iPod to the computer on Windows with iTunes 7.3 or later installed hold down the Shift + Ctrl keys together. This will stop the iPod from auto-syncing with iTunes and the iPod will appear in the source list. Wait until you are sure the iPod has mounted, and that it will not auto sync and then you can let the keys go. This may take between 20 to 30 seconds depending on your computer: iTunes - Keyboard Shortcuts for Windows
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    Your playlists won't be restored by simply connecting your iPod to iTunes.

  • Outlook and iCloud won't sync since Windows 8.1 upgrade

    So I've finally figured out my problem, but have no solution. The problem is that ever since I upgraded to Windows 8.1, Outlook "forgets" that the iCloud add-in is enabled. Every time I start Outlook, I have to manually go into options and re-enable the add-in. After that, syncing calendars and contacts to iCloud and my iPhone works just fine. In order to fix this, I figured out that I can set Outlook to run as an administrator. Works perfectly, as in now having the add-in enabled automatically. I thought this was the end of my troubles, but now Outlook no longer syncs with iCloud. Tried everything, and it just won't.I read on another thread that Outlook won't sync when you run it as an administrator. And sure enough, switching back to NOT running it as an administrator fixed the problem, in that it now syncs again. However, I'm stuck with re-enabling the add-in every time I start Outlook. Is there no other way to do this?

    I don't use playlists. Maybe as a workaround you could try music software other than Windows Media Player, like Media Monkey
    http://www.mediamonkey.com/
    And see if you have better luck.
    The free version of Mediamonkey should  do playlists for you; what you get with the Gold (paid) version, mostly, is an mp3 ripper, but you can also install an mp3 ripper without buying it. 

  • ITunes won't sync music video to my iPhone 3G

    I purchased a music video from the iTunes store and it won't sync to my iPhone. What gives?

    One thing that might help out.
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  • My iTunes won't sync music to my iphone 4

    My iTunes won't sync music on to my iPhone 4. It syncs music on to my ipod 3rd gen, but not my iPhone. All my software is up to date, and all my settings are correct, but nothing seems to work. I've tried, turning my phone off and on, restoring my phone, restarting my computer, unchecking and checking my music, and nothing seems to work. I only have one playist with all the songs I want onto my iPhone, because my whole iTunes library doesnt fit onto it. Another note, it was working perfectly fine yesterday and this morning. But earlier today, my music only showed 3 artists, 2 albums, and 622 songs (which is how much I should have on there), and I tried re-syncing my iPhone, and now there's no music on there at all. Please help, music is the main thing I use my phone for, and its gonna make me go crazy if I dont fix this.

    I know that most of these posts were put up a little while ago
    But.
    I too had a similar problem - my thoughts were:
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    Corruption
    Itunes software issue
    After a LOT of research, I found a simple step that solved this issue for me.
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    It certainly made my life less frustrating
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