I recently bought a new laptop so that I’m not tied down the office desk whenever I need to edit video or some of the other tasks that my iPhone either isn’t capable of performing, or isn’t efficient enough for me to use on a regular basis. I have been contemplating whether I should sync my iPhone to the desktop, or the laptop.
I like the portability of being able to sync with the laptop. I pretty much always have the laptop with me, so if anything ever happened where I needed to restore my phone, or add apps that I have removed previously, I could easily do that. The problem with syncing with the laptop is media. My media library is about 600GB and growing. I don’t have that kind of hard drive space on the laptop, but I’m not sure if I need it. I have about 8GB of music on my main playlist, and occasionally I will add a movie or few TV shows if I know I’m going to be out somewhere like a doctor’s office where I will be sitting with nothing to do, which is rare.
I decided that I would sync everything on the laptop, and just add video to the laptop as I needed it. The process isn’t complicated, but I thought I would write up a walk-through in case anyone needed a little help along the way. Unfortunately I only know how to do this on a Windows machine, as I don’t currently have any Macs available for me to test with.
The first thing you are going to want to do is to make sure you have updated the iTunes software on both machines to the same version. You can check if you have the most recent version of iTunes by selecting “Help” from the file menu, and “Check For Updates” on the drop-down. Do this on both machines. Then make sure your new machine is authorized for the same iTunes account as your original machine (Under the file menu “Store” then “Authorize This Computer…”).
***Note: If you are running a Jailbroken device, make sure you do not download/apply the update to iOS if it is unjailbreakable.***
Then next step it to make sure you have the software on your new machine that you sync with. These programs might include: Outlook (including your backup so that you have all your saved emails, contacts, etc.), SyncDocs, Documents to Go, Chromatic Dragon (ToodleDo Sync), Financial software that you sync with your phone, etc. You don’t want to be without something, so it’s better to take the time and get everything that you had on your old machine put onto your new machine before beginning.
If you are jailbroken, you can use App Backup to backup the settings in your apps. Then sync your device with your old machine, to make sure you have everything synced to the new version of iTunes. Make sure you make have backed up the pictures/video/audio you have taken or bought with your device.
For this step you will need some way to transfer your files from your old machine to your new machine. Email is not going to work well, since there are a lot of files, especially if you are taking your whole library with you. You can use a large thumb/flash drive, an external hard drive, your own file server, some other form of in the cloud file transfer like Dropbox or MobileMe, serve the files via torrent to your new machine, create a public folder on your home network, or any other way you can think of.
Make sure iTunes is closed. Navigate to where your iTunes files are stored on your computer:
Windows XP: C:\Documents and Settings\USER\My Documents\My Music\iTunes
Windows Vista/Windows 7: C:\Users\USER\My Documents\My Music
In this location there is a folder called “iTunes”. You are going to copy that whole folder to your new machine into the folders listed above (assuming you are taking your whole library with you, if not see the tip at the end of the article). If you manually changed where your media is stored on your old machine, you will also need to copy your media from that location. You can check this by opening iTunes and pressing “CTRL+,” (Control and comma together). Navigate to the “Advanced” tab on the right, near the top of the popup box.
If this does not point the above iTunes folder, then you will also need to copy this folder. (D:\iTunes in the example below)

You may need to update your library if you do not have the same username or operating system on your new computer. Open iTunes “CTRL+,” and navigate to “Advanced” click on the “Change” button on the right side of the popup window. Navigate to where you copied the iTunes folder, select iTunes\iTunes Media and “Select Folder” then make sure “Keep iTunes Library Organized” is check and press “OK”. Then iTunes will find your media.
Now you pretty much have everything as it was on your old computer. You can now sync your device to your new computer. I have done this a few times while writing this walkthrough to make sure I covered all aspects, if you see something is missing, please let me know. Also, one of the times I synced with the new computer, it wanted to erase everything and then add everything back to my phone, which I allowed. This will erase all unsaved data in your apps like User Names, Passwords, High Scores, Ect. So be prepared to enter all your info again, if you haven’t used App Backup.
TIP: If you do not want to take ALL your media, you can copy only the media you want via drag and drop from a playlist in iTunes, or Windows Explorer, into the iTunes\iTunes Media folder, and then add it to your library by the file menu “File” then “Add Folder to Library…” and select the aforementioned folder) Before adding the media to your new computer, you will want to open iTunes and select all your media (which will appear in your library, even though it’s not on your computer) delete it. Then add your media folder and add to library.
TIP: If you are transferring your iTunes because you are getting rid of your old machine, make sure you de-authorize your iTunes account on your old machine, as you are only allowed to have 5 authorized computers at a time.
Tested in this write-up:
iTunes Version: 10.0.0.68
iDevices: iPod Classic 5th Gen, iPhone 3GS, iPhone 4
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