How-to: get music, videos, and photos off your iPod or iPhone (OS X)
Know Your Models: The difference between iPhone / iPod touch and other iPod models
Until iPhone and iPod touch came along, all of Apple's media players connected with computers much in the same way as external hard drives: once plugged in, it had no control of its own. That makes media extraction actually pretty easy, as long as you know where to look. Unfortunately, the iPhone and iPod touch are a different story. With those two, the device itself became an active participant, another computer entity that no longer offers easy access to the data -- which ultimately means here that the same methods for copying media that worked before just won't do for the touchscreen-inclined variants. To be perfectly clear, it also means that manually taking media off of iPhones isn't possible, at least ones not jailbroken.
Disabling autosync and enabling disk usage
We've gotta do a bit of house cleaning first. If you've got iTunes installed -- and there's a very, very good chance you do -- we need to make sure autosync is turned off, lest we find ourselves losing those file-laden devices to a refresh. Hold down the Command and Option buttons when you plug in the iPod / iPhone to prevent it from syncing, then from the iTunes menu, click on the device under the left panel.
Make sure you've got "manually manage music and videos" checked as well as "enable disk use," which will come in handy later as it lets the device appear in the explorer as an external drive. Your iPhone will also have a checkbox for automatically syncing -- yep, that needs to remain unchecked.
Copying purchased content using iTunes
This one's easy. All the iPod / iPhone content that you've purchased through iTunes store -- music, video, apps -- can be transferred back to any computer that's authorized with your account. Check Store > Authorize Computer to be sure, and if you've already hit your limit of five (other) authorized devices, you can select "View my Account" and then bring up the iTunes store window to reset them all. Once that's out of the way, simply go to File > Transfer Purchases and let the software do its thing.
Never click "Erase and Sync!" We obviously can't stress this enough. All the content on the device will be wiped clean and whatever's on the computer itself will take its place. That's not at all what you want -- so be careful!
Right click on a track to see the file type. Note that this method also copies over DRM-free iTunes Plus songs.
Copying from iPods / iPhones using software
Of course, if you have non-purchased tracks to transfer, we have a few extra steps to take. We've put a number of different software options through the ringer, and hands down, the one we'd recommend here is Pod to Mac. It works with all iPods and iPhones, jailbroken or otherwise, and any current version of iTunes. And bonus, it's 100 percent free to download and use. Playback can be choppy at times, but it's simple and quick enough to use for transfer to desktop or iTunes library.
Go to Pod to Mac's website and select Download
Locate the file and unzip its contents
Move to applications folder, or wherever you'd like it to stay and be content
Once you start the program, you'll be immediately taken to this page:
The Pod to Mac menu is pretty easy to navigate. All the music, video, audiobook, and ringtones you have will be listed. Click on the specific file you want to transfer, and press either Transfer to Desktop or Transfer to iTunes. Simple and convenient, right? You betcha.
Tip: Copy Pod to Mac onto the iPod itself and have it with you wherever you go
If Pod to Mac isn't your thing, we'd also recommend trying out Senuti and Songbird. Wikipedia has a nice list comparing the feature sets of varoius iPod and iPhone managers, as well.
Copying from iPods manually
The manual copy is a great last resort, and for aforementioned reasons it only works on iPods, but there's some caveats to this method which you'll quickly discover. Make sure you've enabled disk usage (see above), then right click on the iPod icon that shows up on the desktop / under "Devices" in the explorer menu. You should then see the following folders:
Actually, what you probably don't see are those hidden folders -- at least not right away. Unearthing the hidden mysteries on OS X is a bit ticky. Hop into Terminal (under Applications > Utilities) and type in the following commands, one at a time:
defaults write com.apple.finder AppleShowAllFiles TRUE
killall Finder
The first line enables hidden files to be seen on the computer, while the second one essentially force quits finder so that the new command will take effect.
See the folder now? Good. This is where things fall apart.
From inside iPod_Control, Games_RO is gonna be where your downloaded games' content is -- so for example, you can copy the soundtrack from Phase and add to your main library. All audio and video will be found under Music, but here's the frustrating part: all the file names have no apparent relation to the tracks themselves and are organized in a series folders with no apparent pattern. Fortunately, the ID3 tags are still tied to the file so loading it into iTunes or another media player should still give you correct sourcing.
Pictured: Al Green's "Loving You" and a trailer for Watchmen
Manually retrieving photos
As far as images go, for all models of iPod, they're found under the decidedly more public folder Photos, so once you've enabled disk usage, even without showing hidden folders it's pretty easy to find. However, if you haven't checked "include full-resolution photos" under your iPod's Photos tab in iTunes, all you'll see here is a Thumbs folder, which contains the pics in the .ithmb format specifically tailored for the iPod screen. If you're in desperate need of these low-res copies, you can find conversion tools online pretty easily.
A final note: formatting for iPods
Okay, so let's say you had a bit of foresight. If you're planning to switch between multiple platforms, save yourself hassle down the line by starting in Windows and selecting Restore from the iPod's info pane. As with USB drives, while a Windows-formatted iPod can be read by multiple operating systems, the same can't be said for those formatted on Macs. Alternatively, going the more traditional route of formatting it as FAT32 will also work, via any OS, and the iPod itself will make the proper files and folders itself next time it starts up.
With either method, everything on the player will get erased, so if you've got one with important data that isn't readable on a Microsoft machine, make sure to back up what you can on an OS X system first.
Formatting with OS X
Open disk utility, either by searching for it in Spotlight or finding it under Applications > Utilities
Select your iPod (here denoted as IPOD NANO)
Go to the "Erase" tab
Select volume format as MS-DOS (FAT)
Click "Erase..." and then again after you're warned about losing all the data
Note: it should go without saying that if you're iPod's already loaded with music you're trying to save, don't format it.
