Doesn't iPhone sync differently (i.e. they've rewritten it)... i say this because you can use your iPhone while it's docked, and you can't use iPods.

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I noticed this on day one. I really don't like the way the syncing works, you can't drag-drop or anything, aside from this removal stuff.

But, I don't think this is a bug, I think this behavior is by design. I think they did this on purpose becaue they were rushed to get the product out the door.

The sycing is really, really simplistic and only copies what you have checked off. And if you're not connected to the master library, then the files logically don't exist. And then they can't be "synced," can they?

You can't take files from an iPod and move them into your library. We've always known that. Therefore, when "syncing," or making 2 things identical, if something exists on the copy-end that doesn't exist on the master, it gets removed and thus everything has been "sunc."

Cheers,
FL

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I've been having issues syncing my iPhone on iTunes. After activating the phone and syncing the music and videos the phone works fine. However the issue comes when I put the iPhone back on the dock the Mac recognizes the phone but iTunes won't. So I'm not able to change the playlists or contacts on the phone since syncing is not available. I've had to reinstall itunes 4 times for it to work after each time.

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hmm, not on my setup. I keep a very large iTunes library on a Air Disk. I only have a small 150 or playlist I keep on the iPhone. Have run this setup since 6/29 with at least 1 sync/day with no problem.

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I also keep my music library on an external hard drive, but I only sync from a selected playlist (iphone not big enough for all music) and this bug does not seem to affect me...

I have synced a few times without my external connected and have not found that itunes wipes out my library on my iphone - it seems to leave it alone, though it does give me an error message saying that it cant find certain files

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sounds like user error. iTunes would have had to think:

a) the library was empty (i.e. he created a new library in his user folder)
b) the iphone was set to auto sync....a bad idea if you are a "power user" syncing outside the normal home folder. Nice sensationalism though it actually got me to read and comment.

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This also happens with my 1st gen. Shuffle but not my nano or 3rd gen. iPod. Very annoying.

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My 100 gigs of music is on an external drive, and I have yet to encounter this problem. I sync quite frequently without my external library connected -- usually when I want to update the address book, or safari bookmarks.

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As I see it iTunes syncs the iPhone automatically when you connect, or manually if you have it set up that way.

When you tell it to sync specific playlists or songs that are on a connected external drive they'll sync, however once you disconnect that drive and attempt to resync the iPhone while the drive is missing, it won't find the songs so the iPhone or iTunes will assume those songs have been deleted or otherwise removed from your library. Since those songs are no longer in the library iTunes will wipe them from the iPhone because they are no longer in the master library. I believe this is what would happen if you did the same thing with an iPod that you did not manually arrange the tracks on

Look at it this way, iTunes is the master and the iPhone is the slave. If it exists in iTunes and you tell it to be on the iPhone then it'll appear on the iPhone. However if you remove it from iTunes but still have it on the iPhone on the next sync it'll be removed from the iPhone since the iPhone can only currently have what is in the master library. If iTunes can't find the songs then they will not exist on the iPhone, simple as that.

This is the way iTunes works and is not a bug. If you want specific songs on the iPhone then keep them in iTunes otherwise they'll be gone on the next sync. Next time think about it logically when using auto-sync and don't raise the bug flag on a default behavior in iTunes.

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Like I said, I hoped I could describe the issue cogently. Apparently I didn't. Let me clarify.

The iTunes library file lives in my home directory. Only the media files are stored on Airport Disk. So, if I am not at home, then iTunes should just put an exclamation point next to the item in the library. But the playlists I created should remain intact.

When I sync the iPhone, it is iTunes' playlists that get obliterated.

To be clear: I had an old playlist called "Hand Picked" that I was synching with my 2nd Gen shuffle. I wanted a similar list for iPhone since my library is too big. I also thought to create a couple of others just for iPhone. So, I created a folder called iPhone, natch, and put three new playlists in there. I added stuff to those three playlists and set up iPhone to just sync those playlists. A check of iPhone reveals that the sync was a success. If I connect iPhone to Macbook away from Airport Disk, the playlists I lovingly created are vaporized without so much as a dialog box and then the files that were on iPhone after the changes and successful sync are no longer there.

But I have never EVER heard of an iTunes library changing when synching an iPod back to iTunes. Of course it updates play counts and some smart playlists, but nothing destructive. I take great exception to the "user error" comment.

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I have been using my iphone with multiple external and network drives holding the files in my iTunes library and have not encountered this problem in spite of repeated syncing. ITunes is set to sync "selected playlists" each time I plug it in. The only time I need to bother connecting to these other drives is when I'm adding additional media. The stuff on my iPhone has remained intact.

Could Jamie's problem be specific to his Airport drive or maybe an iTunes settings issue? A temporary workaround would be to disable auto synch and only synch music when connected at home which, while it ought to be unnecessary, is reasonably simple as a workaround.

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I keep all of my music stored on an NAS and whenever I'm on the road my phone, iTunes and Macbook don't exhibit that problem. I would imagine this could be more attributed to user error than anything else ... chances are that some setting got changed somewhere within iTunes that has it overwrite everything with each sync.

Either way though, it's definitely weird. Keep us posted on what turns out to actually be the problem (and inevitable solution!) so we know how to counter it if and when it comes up!

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I had a similar problem. 690 gigs of media in an external drive. I load a few playlists and videos. Pick up the iPhone to check it out. All is well.

Sync again, even with the media drive connected, and when I look at the media on the phone, it's wiped. Gone. Vanished. I powered off the phone completely and rebooted it -- and everything was as it should have been: all music, playlists, etc. displayed on the phone perfectly.

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I went looking at my ~/Music folder, and noticed there were two XML files: iTunes Library.xml and iTunes Music Library.xml. The former lists its version number as 7.1.1 while the latter is 7.3.1. My suspicion is that these are in conflict. I moved iTunes Library.xml to another location and will see what that does to help.

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I have done this with my iPhone, as long as the playlist is still there it should be fine, it won't be able to find the songs to play them through iTunes, but it they are still referenced in the playlist you choose to sink then they will stay on the phone.

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Funny that I would check TUAW right in the middle of activating my new iPhone. And I have an external library.

Will I stop the activation? Feck no.

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Actually, the one thing I'm curious about is this: I usually take my external drive with me to work, so if I plug in my iPhone there, it shouldn't have a problem.

However, my work computer's iTunes is NOT authorized to play certain songs that my home computer IS authorized to play. Same library, different computer, different authorization key. I wonder if this will cause problems with the iPhone. I'll post if I find anything interesting.

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i have this issue, I use a separate flash drive for podcasts. Both external drives have the same letter designation. Itunes even says, something to the effect if you sync everything non music you will lose your music... wasn't a big deal, but i have realized my seperate music drive, podacst drive solution currently is outta play.. i know also need to see how to keep 2 sets of outlook contacts (His and hers iPhones)

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I just found a huge list of iPhone bugs at http://www.applehound.com/node/104

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