Updating ipod without losing music

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I am trying to upgrade my father's i Pad 1 to i OS 5 using a brand new Windows 7 profile on my laptop.

When I enable them, i Tunes warns me that by doing that the i Pad content will be by the computer content, which would be absolutely nothing. First, make sure that i Tunes is signed into the i Pad owner's Apple account. Once the update is installed, it will then restore all the prior apps, data, music, movies, pictures and books the tablet. (This is based on my experience upgrading an i Phone 4 from i OS 4 to 5.) Two hours later, a near bricking of the device later, many driver installs and reboots and a couple error codes later, much much clicking later, I now have an i Pad that has "magically" lost 11 GB of data, plus the entire configuration of all the home screens.

To safely reboot your i Pod Touch, follow these steps.

So once again, how do you update an i Pod without losing all the data in the i Pod?

I updated it a while back and needs to be updated again.

The last time I did that, it deleted most of the songs I bought.

An UAC elevation and a trip to the services interface later, i Tunes informed me that if I didn't transfer purchases to my computer I'd lose them, and asked me if I wanted to continue. A cancel and a right click on i Pad → Transfer purchases later, i Tunes told me that the upgrade would wipe the i Pad completely clean and that I'd need to sync everything beforehand, and asked me if I wanted to continue... Upgrading while losing all the data or doing syncronization? The i Pad "tabs" show all sync options are disabled. How can I upgrade an i Pad (or an i Pod) to a newer version of i OS using a brand new computer without losing data in the process? Would a backup include the current version of i OS, making the restoring process undo the upgrade in the first place?

I plugged the i Pad in, and it complained because the relevant Windows service was down.If your computer is using Personal Hotspot on the i OS device that you’re updating, connect your computer to a different Wi-Fi or Ethernet network before you update.

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