How to Transfer My iTunes Library?
September 13, 2014 11:10 AM   Subscribe

My entire iTunes library is on a 2008 MacBook. That computer is running Mac OS X, Version 10.5.8. I’d like to transfer the entire library from that old laptop to my new laptop, a (brand new) MacBook Pro, and to my phone, an iPhone 5c. The problem is that the version of iTunes my old computer is running is apparently too old to be compatible with my new devices, *and* too old for any of the available updates. How can I transfer my library with as little cost and fuss as possible?

I don’t want to transfer anything else from my old computer to my new phone or new computer -- just the iTunes library. When I try the ordinary ways of transferring my library (such as plugging in my iPhone to my old laptop), an error pops up saying that my library is on a too-old version of iTunes and can’t be accessed by my newer devices. When I try to upgrade my iTunes, it says that upgrades are only available for computers running on Version 10.6 or above. Basically *all programs,* it seems like, require a computer to be running at Version 10.6 or above in order to update.

How can I transfer my library over? I have a thumbdrive, but it’s nowhere near big enough to transfer much media from my old computer to my new one, even if the iTunes versions were compatible. I don't have an iPod or an AppleTV. Though obviously I want to spend as little money as possible on this, I’d be open to getting an external hard drive, if that’s necessary – but since the iTunes versions of my old and new computers/devices are apparently not compatible, I don’t even know if loading everything onto an external harddrive and transferring the music and TV shows manually would work?

Oh, and also, in case this is useful info: my iTunes library is pretty much all music and television episodes. There is a fair amount of music on there (around “4 days” worth), most of which I definitely don’t want to lose, because it by and large came from CDs that I no longer have, and I also have at least fifty-odd TV episodes in the library.

As is probably obvious from this question, I'm not very computer literate. Breaking down the process of transferring the library into easy-to-follow steps and being really specific about which updates or equipment I need to buy/get (so I'll be sure not to accidentally try using an incompatible version) would be really helpful. Thank you!
posted by rue72 to Computers & Internet (12 answers total) 8 users marked this as a favorite
 
Thee are two aspects to this. One is actually getting the music files (what I'll call your "corpus") moved over, and the other is getting your playlists, play counts, stuff like that moved over.

The former is easy; the latter might not be easy.

To move the corpus over, the thing to do is get an external hard drive, and after you're done with this, you'll use it for your backups because, sheesh, everybody needs to perform backups. Get a drive with a USB3 interface. Your old Mac supports only USB2, which is a lot slower, but it's compatible. It'll work. I recommend something like this from Other World Computing.

When it arrives, plug it in to your old computer. Navigate through your home directory to Music/iTunes. Copy the whole iTunes directory over to your shiny new external. It'll take a while. Go have a nice cup of tea.

Eject the external drive in the Finder and then physically unplug it. Now plug it in to your new Mac. Launch iTunes on that. Go into Preferences: Advanced and make sure that "Copy files to iTunes Media folder when adding to library" is checked On. You probably also want to have "Keep iTunes Media folder organized" checked On as well. Close the Preferences window in iTunes.

Don't quit iTunes but click back into the Finder and open the external hard drive's window so you can see your old iTunes folder in it. Drag the folder onto the iTunes icon in the dock or into the main iTunes window. iTunes will start the importing process. It'll take a while, although considerably less time than it took to copy from your old computer to the external.

When you're done, you should see all your tracks in iTunes, and you can verify that they are on the new Mac's internal SSD by clicking on any track and hitting command-I (get info). The summary view should show "where" at the bottom, and that should look something like "Users/rue72/Music/iTunes/iTunes Media/…". If it shows something more like "Volumes/external drive/iTunes/…" then the tracks have not been physically transferred to your new Mac, but that shouldn't happen. Assuming everything is OK, you can blank out the external and start using it as a Time Machine target disk.

If you really do need to transfer play counts, playlists, etc, there's more of a process involved, and for all I know, it might not work if the versions of iTunes are too far out of sync. Check out this knowledge base article.

If you've got any iTunes purchases on the old computer, you may want to de-authorize that computer in iTunes before you decommission it. Unless you're keeping it in the family.
posted by adamrice at 11:33 AM on September 13, 2014 [3 favorites]


You can do this without buying an external hard drive by:
- get both computers in the same place, and turn them on.
- make sure that both of them are connected to the same network - like your WIFI at home.
- on one computer, open the 'Settings' app, and pick the 'sharing' icon.
- Check the box next to file sharing.
- take note of the text in roughly the middle of the screen that says something like 'Other users can access shared folders on this computer, and administrators all volumes, at “afp://FRED” or “smb://FRED”.
- On the other computer, in the finder pull down the 'go' menu and select 'Connect to Server'
- in the 'Server Address:' box, type the piece from the other computer that begins 'afp://' i.e. 'afp://FRED'
- You will be prompted for the username and password that you use to log in to the other computer.
- You can then choose the disk you want to copy the files to.

That said, as a computer illiterate person, getting an external hard disk is going to be faster, and more reliable.
posted by wotsac at 11:51 AM on September 13, 2014


Response by poster: If you really do need to transfer play counts, playlists, etc, there's more of a process involved, and for all I know, it might not work if the versions of iTunes are too far out of sync.

I don't think that I need to transfer play counts, playlists, anything like that. I mostly just want to be able to listen to my music or watch my shows on my new computer rather than on my old computer. How the music or shows are organized isn't a big deal to me. Unless there's some reason why it should be?
posted by rue72 at 12:10 PM on September 13, 2014


Get both computer onto your network and make sure file sharing is enabled on both.

Working from your old MacBook, find your new MBP on the network and your account's Public>Drop Box folder.

Move the iTunes Music folder from your old MacBook, and into the Public>Drop Box folder. The transfer may take little while.
posted by Thorzdad at 12:20 PM on September 13, 2014


Caveat: I never used MacOS X prior to version 10.6 Mountain Lion, and the versions of iTunes that I used back then were on Windows, so I cannot promise that:
* I've faithfully represented the description and functionality of your old computer.
* any of this will actually work properly.

Phase 2:
- On the old computer, launch iTunes
- choose 'Preferences' from the iTunes menu.
- Click the button for the 'Advanced' tab in the upper right part of the dialog box.
- Make sure that 'Keep iTunes Media folder organized' and 'Copy files to iTunes Media folder when adding to library' are checked.
- Make a note of the contents of 'iTunes Media folder location'
if the location here is not a subdirectory of your Music folder (the path would be something like /Users/rue72/Music/iTunes/iTunes Media) then you will also have to copy that folder to the disk for copying, and on over to the new computer.
- Click 'OK' to close the Preferences dialog box.
- From the 'File' menu, if the option is present choose an option named something like 'Consolidate Library' or 'Organize Library'. This may be a sub-menu of 'Library'.
Depending on the size of your library and how disorganized it is, this may take a long time to run.
- In one window, go to the Music folder in Finder.
- In another window, open the disk you want to copy your library to.
- Drag the iTunes folder from your Music folder to the new disk.
- It will take some time to perform the copy.


Phase 3: On the new computer:
- make sure that iTunes is shut down.
- Go to your 'Music' folder.
- if there is an iTunes folder there, rename it to 'new iTunes'
- Connect the disk that you are using to copy your library.
- Open the copy-disk in a different window and drag the iTunes folder to your 'Music' folder.
- Once the copy is complete, then Launch iTunes.
- I cannot promise that it will work, but iTunes will probably print a dialog box that says something like 'Upgrading iTunes Library' and it will sit and spin for a while.
- Once iTunes opens, play a few different tracks from different albums to test that you can play music.
- Choose 'Authorize This Computer' from the 'Store' menu to make sure that the new computer can play iTunes Store DRM protected music and TV shows.
- if you are going to sell, gift or discard the old computer, on the old computer, choose 'Deauthorize This Computer' from the 'Store' menu.
- if you have already put some music on the new computer, then:
* choose 'Preferences' from the iTunes menu.
* Click the button for the 'Advanced' tab in the upper right part of the dialog box.
* Make sure that 'Keep iTunes Media folder organized' and 'Copy files to iTunes Media folder when adding to library' are checked.
* Click 'OK' to close the preferences window
* Choose 'Add to Library' from the 'File' menu
* Select the 'Music' folder from the left hand 'Favorites' pane.
* On the next pane right, select 'new iTunes'
* Click 'Open' to continue.
* iTunes will then add the content of the new computer's old 'iTunes' folder to your library.
* Just to be safe, select 'Organize Library' from the 'Library' submenu of the 'File' menu. It will definitely be named this way on the new computer.
* You should now be able to delete the 'new iTunes' folder safely.
posted by wotsac at 12:24 PM on September 13, 2014


Response by poster: Following wotsac's directions, everything goes fine until I get to this point:

From the 'File' menu, if the option is present choose an option named something like 'Consolidate Library' or 'Organize Library'. This may be a sub-menu of 'Library'.
Depending on the size of your library and how disorganized it is, this may take a long time to run.

When I do this, everything seems to go well and it seems like it's about to start running -- but after about one or two seconds, an iTunes error pops up and says, "There is not enough room on "Hard Drive" to copy all of the requested files."

I've tried going back and doing the whole process all over again, multiple times, have shut the computers down and turned them back on, etc, but this happens every single time. I don't want to copy the files onto the Hard Drive, I'm not seeing where I even commanded the computer to do that...? Is there a way to fix this problem?
posted by rue72 at 4:01 PM on September 13, 2014


Will the place you bought the new computer from do this for you? I know apple used to.
posted by cestmoi15 at 4:18 PM on September 13, 2014


Ok. The consolidate process copies all of the files into one place. Are there files on your old computer that you can delete? Have you emptied the trash recently?
posted by wotsac at 5:22 PM on September 13, 2014


Response by poster: The trash is empty, and there's nothing to delete on that computer that I can think of. I mostly used it for word processing, the internet, and watching TV/listening to music. (Now it's my mom's computer, but she's using it for the same kind of thing).

The TV shows tend to take up a lot of room, I think -- but I've already deleted as many of those as possible in order to make room for the ones I care about. What's left is the stuff that I don't want to get rid of if at all possible, and that I want to transfer over.
posted by rue72 at 5:36 PM on September 13, 2014


Let's try skipping the consolidate step and see how it goes. But the purpose of that step is to make sure everything is actually in your iTunes folder, so it's possible you may not end up copying everything.
posted by wotsac at 6:03 PM on September 13, 2014


If the TV shows are ones that you purchased from the iTunes Store, you can delete them and re-download them at any time. You can confirm this by going to the Purchased section of the iTunes Store app on your Mac or iPhone.
posted by Rock Steady at 8:48 PM on September 13, 2014


Have you tried iCloud? I signed up for it last Christmas. $25.00 a year and it holds everything, all my pictures and music. I really love it.
posted by myselfasme at 10:11 PM on September 13, 2014


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