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Possible bug with iPhone synching and external iTunes libraries

TUAW reader Jamie Phelps has possibly stumbled upon a nasty iPhone synching bug when keeping one's iTunes library on an external hard drive. While tips like our how-tos for setting up iTunes with external drives or even an AirPort Disk work pretty well even when synching iPods with them, Jamie found that his iPhone gets the brainwash treatment when he's away from the drive containing his external iTunes library. As the story goes, Jamie synched his iPhone with a few songs and playlists, made a couple new playlists and then synched again. Hitting the road, however, and getting away from his external iTunes library drive is when the bug rears its nasty head: plugging the iPhone in while on the go caused iTunes to wipe out the new playlists and songs from the second sync operation, basically reverting them to their state before the second sync. To verify, Jamie even got adventurous and tried this whole thing a second time, once again watching iTunes blow away changes from the previous iPhone sync when the external media library isn't mounted.

This is the first time I've heard of iTunes handling this kind of setup in a poor way; for as long as I can remember, iTunes has been clever enough to realize what's happening and and would either not sync anything to an iPod when away from the library drive, or it would actually sync any media downloaded or imported while away (as we've mentioned before, you can use the Advanced > Consolidate Library command to move all this new media once reconnected with the library drive). Since we don't really have any evidence of Apple deliberately changing this behavior for their iPods or iPhones, it makes sense for this quirk to be classified as a bug that will hopefully be squashed with an inevitable iPhone software update. But what say you, TUAW readers? Anyone else get bit? Sound off.

TUAW reader Jamie Phelps has possibly stumbled upon a nasty iPhone synching bug when keeping one's iTunes library on an external hard...
 

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Nick Ellis

David, please help me. I have my music in an external drive, and I made a sync with this drive turned off, so now iTunes thinks the iPhone is full, and it says that it does not have the space to copy the songs, and I can't delete them since they don't exist. This is the biggest bug I've ever found on iTunes or iPhone for that matter.

I know I can make a restore and start again from scratch, but I wish there was another option. Someone please help me!

September 18 2007 at 7:07 PM Report abuse rate up rate down Reply
Jamie Phelps

Looks like the old iTunes XML file was the culprit. I'm not getting this issue anymore.

July 16 2007 at 12:30 AM Report abuse rate up rate down Reply
Andrew

I'm not sure how you guys are getting this glitch. I keep my 70+gb iTunes library on a 160gb WD Passport that I usually carry around with my Macbook Pro. The iPhone has it's own set of smart playlists that sync to it, and yes, it does autosync on connect.

If my hard drive is disconnect when I try to sync, it just gives me an error message saying it can't find the specified files, but it removes nothing. I have been constantly getting new phone numbers sync I switched from Verizon to AT&T now, and every connect, iPhoto pops up asking if I would like to "import x images" and another prompt pops up detailing that I have x amount of new contacts and if I would like update my address book.

Are you fellows that are having issues using windows based PCs or Macs?

I have yet to have any odd glitches, I just accidentally call people when I am updating my address book at times.

July 15 2007 at 2:17 PM Report abuse rate up rate down Reply
Jen

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

July 15 2007 at 11:19 AM Report abuse rate up rate down Reply
noneother

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)

July 14 2007 at 9:43 PM Report abuse rate up rate down Reply
punkassjim

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.

July 14 2007 at 9:05 PM Report abuse rate up rate down Reply
punkassjim

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.

July 14 2007 at 7:59 PM Report abuse rate up rate down Reply
Collin Ruffenach

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.

July 14 2007 at 7:54 PM Report abuse rate up rate down Reply
Jamie Phelps

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.

July 14 2007 at 5:06 PM Report abuse rate up rate down Reply
Alex

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!

July 14 2007 at 4:56 PM Report abuse rate up rate down Reply
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