I've been successfully using my iPhone and syncing it to this computer for a long time. In fact, right now, I can press the sync button and it correctly updates my Outlook contact list and my Notes in the iPhone.

In the past, I had always opted to manually manage the music and videos on the phone. (The checkbox in iTunes "manually manage music and videos" was checked.) Worked fine. I could drag songs directly from the hard disk onto the phone and they would work.

Recently, I was having trouble with my computer taking forever to boot up when it was connected to my corporate network. I finally realized it was because of a gigantic user profile, because applications keep stuffing large things into the user profile folder that they shouldn't be. So I cleaned out a bunch of huge stuff out of there, including all the music in the itunes folder in the profile (it was a different set of music than what was on the iphone anyway), all of the huge backups of older versions of the iphone firmmware, older backups of the iPhone itself, etc. This, combined with other cleaning out of my 4+gig user profile, got my computer to boot at a normal speed again.

But now, in iTunes, the "manually manage" checkbox has somehow become unchecked. In fact all the checkboxes are unchecked except the ones that sync my outlook contacts.

Because the "manually manage" checkbox got somehow unchecked, I can't drag any new songs onto the iPhone or do any editing of the songs that are on the iPhone already. They are all grayed out.

When I try to check the checkbox to "manually manage", it says it's going to completely erase the iphone. NO!!!!! NO!!!!! NO!!!!! I had *already* manually managed this iphone, and I just want to keep doing it now. It's critical that I don't erase it right now.

How do I check that checkbox without erasing the iphone?

All my google searches either say:

1. Just check the checkbox and all is well. Those posts don't seem to talk about the erasing part.

2. They say you have to erase it because it was originally synched with a different computer. This is not true, it's only ever synched with this computer, and it was ALWAYS set to "manually manage" for its entire life.

Help?

How about in the interim you grab some third party utility to back everything up?

It does sound like some preference file was damaged or deleted while you were purging your profile folder.

There's this thread: http://en.kioskea.net/forum/affich-105068-itunes-wants-2-delete-all-my-songs


BTW, the odd thing is that I recall a prompt to erase when you set up AUTO sync, but not when you choose to go manual.

Have you tried creating another user account with its own set of iTunes prefs and then taking a look at this from there?

Aha, that might be it. I think that, among the things I did to speed things up, I copied the slow account profile to a new account profile and began using that. It's this new user account profile (with the data copied from the old one) that's causing the iTunes trouble.

Interestingly, everything else works including Outlook synching.

Nope. This is definitely when I'm *enabling* the manual sync check box.

This is one of the most infuriating things about iTunes. I hate how it insists on erasing the iPod/Phone. I ended up getting software from Purple Ghost to back my stuff up every time iTunes insists it needs to wipe my iPod. It wouldn't be so bad if you could redownload all your purchases from iTunes, but I haven't been able to figure how to if you are able.

You can definitely get back all your purchases. I've never done it, but that's because I don't really buy anything from the iTunes store.

Tony, let us now what happens when you look at the problem from a user account with clean iTunes prefs. From what I recall, you should be able to move to a new computer without formatting an iPod/iPhone, so you should also be able to go to a new user account - just set it up to connect to the iTunes store with the same credentials you've always used.

Hm, that doesn't seem to have been it. When I go into the "Authorize this computer" screen it says that I have already authorized this computer. (So in theory it should all be fine. So what the fuck?)

So it's not that it thinks I'm on a new computer. That's not the problem.

Perhaps iTunes is poor with regard to its handling of differing user accounts. Perhaps they've only accounted for the condition of a reformatted computer, not a changed user account. They don't seem to understand that you can have more than one user account on the same computer.

In the meantime, I'm working around it by using CopyTrans Manager to manage the songs on my iPhone and to transfer songs to it manually. iTunes is now relegated to being an outlook-contacts-synchronizer only.

I didn't mean that it thought the computer was new. Just that your prefs had somehow been trashed/damaged in a way that it was acting in a non-default capacity. Setting up a brand new account and running iTunes for the first time on that account would help verify this and might actually "just work."

I just *did* create a new user account.

Checking iTunes troubleshooting: I can produce the same effect as creating a new user account by simply deleting a couple of itunes prefs files that exist within it. I'll try that.

Nope, that didn't do it. Got a lead on something else. Trying...

Okay, I think I might know what happened.

At some point when I was trying to clean up disk space in my user profile, I pressed the button on the iTunes which said "RESET SYNCH HISTORY" because I thought it would clean up space in the user profile.

But now that I look at that button, it also says:

Maybe that's why it's so adamant about erasing the ipod? It says something to that effect.

I have used the reset sync history before on my manually managed iPhone and it didn't insist on deleting my music on the next sync. So it can't be quite that simple.

Hm. This looked promising but did not help:

http://kb.iu.edu/data/aril.html

You should be able to lose your computer without losing what's on your iPod. Even if only using iTunes.

Exactly. So WTF, Apple?

Maybe I'm missing something maybe we're all missing something. But I'm pretty confident that what you're seeing is some bug or other gaff that is not normal behavior.

That setting should be part of your iPhone and not the software installation. I mean, if you connect that iPhone to a new computer it should be able to show you the setting as it was set and preserved on that particular phone. It's like in this case that setting has somehow been reset. However, I still believe it's not supposed to format your phone when switching from automatic to manual.

But it does.

Or, at least, it tells me it will if I go through with it. I haven't actually gone through with it because I don't want to erase the phone.