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What do you mean "how to upgrade an iPad"? You plug it in, start iTunes, click Upgrade and that's it!

That's what I thought before starting the process. After all, it's Apple we're talking about, right?

Not quite.

I am trying to upgrade my father's iPad 1 to iOS 5 using a brand new Windows 7 profile on my laptop. I plugged the iPad in, and it complained because the relevant Windows service was down.

An UAC elevation and a trip to the services interface later, iTunes informed me that if I didn't transfer purchases to my computer I'd lose them, and asked me if I wanted to continue. Continue to what, upgrading or transferring?

A cancel and a right click on iPad Transfer purchases later, iTunes told me that the upgrade would wipe the iPad completely clean and that I'd need to sync everything beforehand, and asked me if I wanted to continue... doing what? Upgrading while losing all the data or doing syncronization?

Now I'm stumped. The iPad "tabs" show all sync options are disabled. When I enable them, iTunes warns me that by doing that the iPad content will be replaced by the computer content, which would be absolutely nothing.

So, here's my apparently simple question. I'm really surprised I have to ask...

How can I upgrade an iPad (or an iPod) to a newer version of iOS using a brand new computer without losing data in the process?

Is a backup what I want perhaps? Would a backup include the current version of iOS, making the restoring process undo the upgrade in the first place?

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Well, the good news is that once you finally upgrade to iOS 5 it can self update from there. –  CyberSkull Dec 25 '11 at 20:11
    
@CyberSkull I can't wait to banish iTunes from my computer. –  badp Dec 25 '11 at 20:13

2 Answers 2

In addition to iTunes syncing, iCloud allows a backup and then you can restore it to the same device or another. It can be backed up anywhere there is WiFi I believe.

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First, make sure that iTunes is signed into the iPad owner's Apple account. It is best if this is done in a separate login account on the computer so you do not loose any of your saved apps and backed up data.

Then from there once you plug it in to a full backup to the computer, no upgrading yet! Always do a full backup before an upgrade. Once backed up go and do the upgrade. This will wipe all data on the iPad! Once the update is installed, it will then restore all the prior apps, data, music, movies, pictures and books the tablet.

After that, everything should be golden.

(This is based on my experience upgrading an iPhone 4 from iOS 4 to 5.)

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So restoring the backup won't also restore iOS 4 with it? –  badp Dec 25 '11 at 20:18
2  
@badp I recommend doing the double backup method. There seems to be a backup during install, but doing a backup beforehand makes sure. –  CyberSkull Dec 25 '11 at 20:20
    
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 iPad that has "magically" lost 11 GB of data, plus the entire configuration of all the home screens. I can't even bring myself to downvote you, because it seems this is just how things are supposed to work?! I'm so confused and worried and disappointed right now. –  badp Dec 25 '11 at 22:49
    
@badp I'm sorry it didn't work out. –  CyberSkull Dec 26 '11 at 1:18
    
Thank you, I don't think it's your fault tbh –  badp Dec 26 '11 at 8:27

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