IPhone sync to iTunes library has free space issue

The iPhone “~’s iPhone” cannot be synced because there is not enough free space to hold all of the items in the iTunes library (additional 69.9 MB required).
I have 239 GB available on my MacBook Pro running OS 10.7.5 with iTunes11.1.2 and iPhone 4 running iOS 6.1.3 and the memory nearly full — 57.2 MB Available. This now happens over 50% of the time. These two issue might be related. If the error statement is misleading, that should be fixed.

OK, I deleted a bunch of pictures and it completed.
Instead of "The iPhone “~’s iPhone” cannot be synced because there is not enough free space to hold all of the items in the iTunes library (additional 69.9 MB required)," I think I'd have understood it effectively if it were "The iPhone “~’s iPhone” cannot be synced because there is not enough free space to copy all of the items into the iTunes library (additional 69.9 MB required)." What a difference two words can make.
Who know how to get this across to Apple, Inc?

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Iphone4s cannot sync to itunes not enough free space

I keep getting the error message below & need some help
iPhone4S
iTunes 10.7.0.21 (which I updated yesterday) on Dell Inspiron N5040 running Windows 7
"...cannot be synced because there is not enough free space to hold all of the selected items (additional 14.93 GB required)"
I transferred all my purchased music & video from my iPhone to my iTunes Library, deleted the files & restarted both my latop & iPhone
Connected iPhone to iTunes & seleted Manually Manage Music and Videos
Go to Music tab & when I select Sync Music to pick the music to sync, I get a message asking to Sync Music, which when I do, before seleting any music, my capacity bar shoots to "all blue" & over capacity
What am I doing wrong?!?

Hello bruf,
I found a resource that I feel has the best chance at isolating, if not resolving the issue.
iOS: Troubleshooting backup issues in iTunes
http://support.apple.com/kb/ts2529
Here is a general over view of the troubleshooting to be done:
Resolution
Simply restarting the computer and the iOS device may resolve a backup issue. After restarting, attempt to restore again. Learn how to restart your iOS device.
To perform the rest of steps in this article, you need to be logged in to the computer as an administrator. If you're not sure if you have administrator access, contact the owner of the computer or the system administrator.
Collapse All Sections | Expand All Sections
1. Back up your backup
2. Update to the latest software
3. Disconnect other USB devices
4. (Windows only): Check for Layered Service Providers (LSPs)
5. Check security settings
6. Back up using a new user account
7. Reset the Lockdown folder
8. Windows only: Update your USB chipset drivers
9. Back up on a different computer
All the best,
Sterling

My iPhone 4s in iTunes shows incorrect free space!

Okay, this is very odd... when my iPhone 4S is plugged in, it says that I have way more free space than should be available? What in the world is going on? I wished I had the 64 GB iPhone, but I don't. It seems to incorrectly calculate my free space on my iPhone 4S repeatedly. I am doing a restore of my iPhone right now, hoping that will address the issue. Now I do have iTune Match turned on and am wondering if that has something to do with this? It seems to get confused with what I had on my iPhone and what is in iTune Mactch. I only saw this after doing the iTune Match thingy.

Hey - did you get anywhere with this?
I have the exact same problem and it is definitely related to iTunes Match (I enabled 24 hours ago and the problem started immediately).
In my case the actual phone displays the correct information (about 1.3gb free) but via iTunes (either connecting over wifi or over usb) it displays 19.4 gb free.
In my case the difference is almost exactly the size of my iTunes library.
Here is what I belive is happening (no fix yet).
I have enabled iTunes Match on my phone but I have left the song files on the phone (i.e. I play files actually from the device and not from the cloud) . Now, when I connect to iTunes, iTunes sees merely that iTunes Match is enabled and therefore belives that the phone does not contain any downloaded music (or at least did not contain any at the point iTunes Match was enabled) and therefore displays a library-size chunk as free space.
One fix which I suspect would work would be to delete my entire library from the iPhone, enable itunes Match and redownload the entire library from the phone. That however is not something I want to entertain at present.
This has to be a bug at Apple's end - I hope they fix it soon!

I just purchased a Macbook, iPad, and iPhone and I am trying to sync my iTunes library from my Windows laptop. How can I sync my iTunes library to all devices?

I just recently purchased a MacBook Pro (13 inch with Retina display), an iPad Air 2, and an iPhone 6 plus. Before these purchases, I was using a Windows 7 laptop to manage my iTunes library and iTunes purchases. I am in need of syncing my iTunes library on my iPod classic (160 GB) with all of my new Apple devices. How can I sync my iTunes library with all of my new devices?

Devices can only sync to one library at a time. You can, however, have multiple copies of libraries on different computers though it can be tricky making sure they are always synchronized. You can put your Windows iTunes on your Mac.
Moving a library: Quick answer if you use iTunes' default preferences settings: Copy the entire iTunes folder (and in doing so all its sub-folders and files) intact to the other drive. Hold down the option (alt) key (shift on Windows) and open iTunes. At the prompt to create or choose a library choose the copied iTunes folder.
When this is to a new computer put the copied iTunes folder in the default location of Macintosh HD > Users > *User Name* > Music then you don't even need to start with the option key held down, iTunes will automatically look for it there. (Make sure there isn't anything already in the iTunes folder there that you want to keep since you will be replacing it with the one you are moving.)

How can i sync my iTunes library from my iPhone with my new mac mini

Recently my hard drive failed on my mac mini. I had burned a bunch of CDs on the old mac mini and then sync'd it with my iphone. Now the CDs are on my iphone but not on the new mac mini. How can I sync my itunes library from my iphone to my new mac mini?

The iphone is not a backup device.
You need to copy everything from the backup copy of your computer computer to your new one.

HT4623 trying to sync my itunes library to my iphone 5 not happening. please help.

trying to sync my itunes library to my iphone 5 not happening. please help

Are you using iTunes 10.7? (This is required to sync the iPhont 5.) If so, what happens when you try to sync your phone? Any error messages?

My iTunes library has been replaced with my husband's iTunes library on our iMac. How do I get my iTunes library from my iPhone back onto my iTunes library on the iMac?

My iTunes library has been replaced with my husband's iTunes library on our iMac. How do I get my iTunes library from my iPhone back onto my iTunes library on the iMac? Help!!!

Well, this is a problem, because the only material you can transfer from your iPhone (using only Apple software) is material you purchased in the iTunes Store.
To do that, plug your iPhone into iTunes, then choose File > Devices > Transfer Purchases from iTunes' menu.
Generally speaking, you should restore your iTunes library from your computer's backup.

I cant sync my iphone from my itunes library, i get an error message saying there are problems and songs cannot be located.

I cant sync my iphone to my itunes library, I get an error message saying there were problems and songs won't be
uploaded. "songs not found, would you like to locate?"

http://ipod.about.com/od/itunesproblems/qt/Fixing-The-Itunes-Exclamation-Point.h tm

HT1711 There is a preference for syncing my itunes library to my iphone (4s). How do I "sync only marked items"?

There is a preference for syncing my itunes library to my iphone (4s). When I first synced, it asked me if I wanted to sync everything, but that is too big for my memory. How do I get back to that window and "sync only marked items"?

Great.
Thanks.
The problem was that my iphone was not coming up in my devices list....different socket...better result.
Thanks again.

Hi Apple, Is there a way to move some of my less frequently used music out of my iTunes Library to free up some space on my full hard drive but with the option to re-add it later?

Hi Apple, Is there a way to move some of my less frequently used music out of my iTunes Library to free up some space on my full hard drive but with the option to re-add it later?

Hi Apple, Is there a way to move some of my less frequently used music out of my iTunes Library to free up some space on my full hard drive but with the option to re-add it later?

HT1391 All the music in my itunes library has vanished apart from the purchased items? why has this happened and where has it gone? It is no longer on my iphone or on my computer??

All my music in my itunes library has vanished apart from the purchased items! It is not in the music > itunes > itunes media folder, I've searched the entire system for mp3 and nothing. Why has this happened and where has it all gone?

http://support.apple.com/kb/HT1329

TS1368 I cannot sync my iTunes library to my iphone 5 can you help I get error message connection could not be established to iPhone

I cannot sync my iTunes library to my iphone5 can you help I get error message a connection could not be established to the iPhone

Yes it is.
Initially I got an error message saying can't connect because of Date & Time settings.
Went in and re-verified that those were correct.
Tried to update downloads and then got a new error message: "Can't connect to iTunes Store".
I live in the US and that's where I created my iTunes a/d and Apple ID.
I am currently in India --- can that coause confusion re date & time?

Multiple iPhones and one iTunes Library

I have a question about multiple iPhones and one iTunes Library.
Currently I have 3 PC's, 2 iPods and 2 iPhones.
My PC had the iTunes library on it and everyone was just listening to mine via the iTunes sharing.
Well I bought a Buffalo LinkStation and told itunes to move my library to M:\My Music\..... and then did a Consolidate Library which in turn moved all the music from my C: drive to the M: drive.
My wife's computer has it's own Library with no music (only app store apps, and ringtones).
Now my question is what happens if I tell my wifes computer that M:\My Music\....... is her new location of the library and restart itunes. I am pretty sure this will work fine. But what happens if she syncs her iPhone now? Will all my apps now be on her phone and she will lose hers? She does have her own itunes store account with her own apps. Is there a way to have it so only her apps are on her phone and my apps are on my phone? Can she choose different playlists to be synced than what I have?
Any help would be appreciated.
Thanks
Brad

Since the three of you are using separate iTunes accounts, then you each need to run your own itunes, which should be logged into the itunes store using each individual account. For that, on a laptop, you each need to have your own computer accounts.

ITunes library has lost the past year's worth of content, but the files are still in the directory

Help! How do I restore the past 11.5 months' worth of content to my iTunes library?
Well this is weird. Suddenly my iTunes library has lost everything added since late January 2014 - almost a year's worth of content. Podcasts, audiobooks, iTunes purchases, MP3s bought elsewhere and imported, movies, TV shows - all gone. Apps added in the past year also seem to be gone, although apps acquired before then have the most current update. As far as I can tell, all of that content is in the file directory structure - it's just not in the iTunes library system.
Curiously, the "last played" data all seems current, except that many of the more recently played songs have gone missing; tracks that were modified in the past year, but were added in 2013 or before, are still listed as being modified in 2014. Anything changed in the past year remains changed; but anything added in the past year simply isn't there.
I have no idea what caused this. Earlier today iTunes crashed for random reasons, but that happens every week or two anyway; and for that matter this issue could have developed a couple of days ago, and I just didn't notice it. (I'm sure it can't be older than that - I would have noticed.)
I've got good Time Machine backups, but I'm not sure how to go about restoring this - I suspect that this help page tells me the steps I need to take, but I'd like to have some confirmation before going through those steps. (And that procedure doesn't involve Time Machine anyway, right?)
Theoretically I suppose I could also go through my directory and add the files to iTunes, one by one, but it would be extraordinarily complicated to figure out what needed to be added. I'd also like to get back all the metadata - played, unplayed, play count, last played, and so on.
Restoring the files from Time Machine doesn't seem to make sense to me, because the files aren't actually missing. Would restoring an iTunes Library.itl file help at all?
Thanks in advance!

Hm ... I guess I can't edit the post above. Anyway, I seem to have solved it by ...
Quitting iTunes.
Going into Home / Music / iTunes, and renaming the file "iTunes Library.itl" to "iTunes Library (corrupt).itl".
Entering Time Machine, and restoring the "iTunes Library.itl" file from a few days ago. I went back two days, which seemed far enough back to be "before" the problem but not far enough back to have trouble with recent acquisitions.
Re-opening iTunes - and everything seemed to be back in order.
So that's fine for now. We'll see if the solution is stable.
Very, very tentative assignment of blame: I believe iTunes crashed earlier today after I'd synced photos from my iPhone to iPhoto, and then iTunes crashed while iPhoto was closing (and taking its sweet time doing so). If that was indeed the case, that's at least the second time in the past couple of months that trying to sync iPhone photos to iPhoto has caused me significant problems. (The last time led to 80% of my iPhone suddenly being occupied by "Other", and a full restore of the darn thing.)

My itunes library has mostly vanished

My itunes library has mostly vanished, but is still on my iphone. How do i sync it back to itunes without removing it from the device?

See Empty/corrupt iTunes library after upgrade/crash.
tt2

IPhone sync to iTunes library has free space issue

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