Unfortunately, this is not as easy as it should be. The sync appeared to go fine, but there were no apps or anything when restored to his iPhone 5. Going into the sync settings in iTunes offers an option to turn on app syncing, music syncing, etc, but alarmingly doing so would have completely removed the existing apps, music, etc on his 3GS.

Turns out that the only way to get iTunes to download the apps and other content from the 3GS was to right-click on the device in the sidebar and click "transfer purchases". I actually had to look up how to do this because that function is completely non-obvious.

Why is this the case? Why can't Apple be smarter and have iTunes download all information from the iPhone upon connection? My Palm m100 I had a decade ago managed this just fine - I could HotSync to a computer that I had never used before and it would dutifully sync contacts, calendar, etc, and make a full backup of the device. Also, shame on Apple for making it so easy to wipe the apps, music, etc off the phone during the process of trying to back them up. I hate to think that he might have lost everything, or been completely unsuccessful moving to his new iPhone just because of these stupid sync restrictions.

It sounds like your co-worker said no to this in the past, and checked the box to not pop up the message anymore.

I set my iPad up (and my new iPhone) without iTunes at all. iCloud backup let me move from an iPhone 4 to 5 without a USB cable at all and all my data moved over perfectly.

I plug in to my computer to transfer videos that don't transfer using Photostream. I also occasionally will do a sync of movies for a trip.

Music is iTunes Match. Photos are Photostream. Email is IMAP. Contacts/Calendars/etc is iCloud.

It actually works very well and I'm able to move to new devices or restore from a backup without issues.

No iTunes is the answer!

I would imagine this is because the iPhone/Pod/Pad is expected to be a slave not a master.

When I hook my iPhone up to someone else's computer, it asks me if I want to overwrite everything on the phone with that data, not upload my data over theirs. Indeed, with purchased data going up from a phone the computer should need to be authorised etc first.

Whilst I accept that what you wanted to do should be simpler and more intuitive - I would be very unhappy were it automatic.

Why would this always be the case? I'd expect the mobile device to have more accurate/newer information than the stationary device, most of the time. If you're networking at lunch or a conference, and you put all that info into your phone, why wouldn't that be synced with the PC instead of the other way around?

iOS5 changes it more over to the iOS device though

One of those is the backup not being from the same iOS version. It will let you restore it to a new device, but then it doesn't complete (ie apps and such).

Just went through this going from an iOS 5 iPod Touch and an iOS 6 iPhone 5. The downside is that it makes old devices like the iPad 1 (which can't run iOS 6) going to say iPhone 5 (which can't run iOS 5), impossible to restore.

iOS: Transferring information from your current iPhone, iPad, or iPod touch to a new device http://support.apple.com/kb/HT2109

You set the problem up like this, person comes to you and wants to buy lunch. You put down a "Chutes and Ladders" game (minimum age 3) and you say sure as soon as your piece wins. Now wait and watch them. If they do anything that isn't in the rules you play a loud buzzing sound and scold them.

The thing is that "Chutes and Ladders" is like the simplest game ever, but when you combine "I'm trying to do X" with "Your trying to force me to learn Y". A number of people's brain just freezes up. I don't know if that is like some deep psychological principle but the fact that doing "Y" is totally unrelated to trying to get "X" done its like your brain refuses to allocate any cycles at all to learning Y. What is worse people get emotional and angry because dammit they want X and before you blocked them they knew how to get it.

We forget that as children when things were 'new' we expected to not know how to do them. But when we are set in our ways that level of change is much less tolerable. In a lot of ways all sorts of technology is like that.

One strategy I've had some success with is to take people who aren't trying to do anything with the new technology yet and just explore it with them. That goal of exploring allows them to ingest new concepts, and then when they try to do something with the technology some of those 'learn the game' concepts will already be in their brain.

So you should try the test (or try it on an unsuspecting test candidate) my experience has been that no matter how 'simple' the game is, the fact that it seems completely orthogonal to the person, their ability to 'shift gears' and learn a new thing so that they can get on with the desired thing is blocked. It is especially true if you put a time limit on getting the desired thing done.

The challenge is that a number of things seem to have an assumption about your basic skills that may not be valid. An acquaintance went nuts when an app required that he cut and paste something on his phone. He had never had a reason to do cut and paste before so to complete the task he had to learn cut and paste. He was making zero progress on that goal. I did it for him, then later went back and showed him in a non time-constrained / outcome-desired setting how to do it. That worked fine of course, and now its part of his tool kit.

A lot of the "techie" stuff like backups and restoring that Marco describes here is solved with a Chromebook. And it uses familiar user interface paradigms that people recognise from their experience using Windows (especially now that they added the windows management system that looks a lot like Windows 7), whereas the iPad has completely new paradigms that people transitioning from a computer will find strange and foreign.

Many people I've introduced to iPads and Android devices have ended up not really using them because they're much more familiar with the point and click windows-based desktop system of Windows than "apps".

Not that the Chromebook fixes everything. But Google has done a great job identifying some important problems with the way our technology works today and is trying to get rid of those problems or make them irrelevant by providing you with a device where you really don't have to worry about hooking it up to your PC to "sync", update the system OS version, figure out the settings for something techie and confusing, or use iTunes (my God, iTunes) to do anything.

Can you imagine what a Chromebook-iPad hybrid device could be like, with the automatic updating of Chrome, syncing system of Chrome, familiarity of Chrome, but the polished user experience and app ecosystem of an iPad?

Once that is the case: that I can get an internet connection from dawn until dusk, no matter where in the country I travel, or heck even what country I travel to then I would absolutely get a Chromebook. But we aren't there yet.

And I'm seeing people living in the country-side, on farms, talking through Skype to their relatives that live abroad, using an USB stick that's connecting them through 3G, or using a broadband 50-100 Mbps connection exposed through Wifi. It's totally shocking, given that some of those places do not have access to cable TV (only through satellite) or to basic utilities such as marsh gas pipes, yet they have Internet access.

Of course, right now Internet access is a problem, even for us sometimes. The costs of my 3G connection is enormous when in roaming. Sometimes you lack the signal and 3G connectivity is not available everywhere, etc... but in 5 years from now I believe it will be a non-issue.

And Chromebook is designed for the long-run and I hope they won't cancel it in the wake of Android's success.

There are Chrome apps that are designed to also have functionality when offline, albeit limited. For instance there is a GMail app in the Chrome store that's designed to work in offline mode [1]. It's really basic and not something I would use, being more like a demo at this time.

I was also sad to hear that Google Reader is not working in offline mode anymore, so now for my iPad I'm searching for a replacement, and because what I've found in the store seems to suck, I may even code one myself - although I may just forward new items to my email address and do some filtering in my email client.

[1] https://chrome.google.com/webstore/detail/ejidjjhkpiempkbhmp...

I don't agree: 1) The bandwidth is a limited resource. 2) You can't install senders in every corner of everything to cover blind spots. If you haven't experienced both I believe you're using your 3G almost always without too much moving around and in the area without too much heavy users.

If you need to rely on the device, sorry but it's local apps + synchronisation or bust.

Centralised computing works fine if your kit is in the office and your clients are in the office and your operations team are shit hot. Otherwise - it's totally retarded.

Some of our corporate clients even have a direct fiber connection to us as they don't trust the Internet not to screw up.

This is reality.

When I left I decided to delete my email account because why would I need it anymore. So I remove the account from the iPhone and went to eat a bagel.

Imagine my surprise when I come back to my phone to call my sister except iPhone tells me I only know about 8 people.

Apparently the iPhone tied all my contacts with the company account so when I deleted that, there went all my contacts with it.

No problem right, I'll just retrieve my backup from my computer from the last time I synced and I'll get my contacts back and then I'll figure out how to transfer over the contacts.

Except apparently when I got this phone with iCloud it turned off backups when I synced with my computer. Okay no problem, iCloud should have it right?

Except iCloud has been telling me that it doesn't have enough space to backup my stuff for weeks. I just assumed that meant my apps weren't getting backed up, which is fine. But apparently they don't update anything else, even if you've already backed it up (this is definitely not all Apple's fault, but iCloud is pretty confusing about its backup rules). Not sure why I couldn't retrieve my contacts from right before when I deleted them but they were no where to be found.

So finally I just bit the bullet and synced with an old backup and lost about 3-4 months worth of text messages. Yay.

Gone were all my contacts and calendering data, including birthdays.

I had to export my stuff to CSV and massage it in local Outlook and do some reverse-and-double-wipe sync stuff through iTunes.

It was horrible and I refuse to buy another iDevice ever again.

This kind of behaviour is probably something businesses like. Info on company servers stays on the servers.

This isn't an "iDevice" issue, it's a data ownership issue.

Definitely agree with the larger point though. PCs (phones, tablets, etc) are ridiculously hard to use and unreliable even if you kinda sorta know what you're doing.

Wait but "Updating to iOS 5 will delete all of the apps and media... To preserve your content, apply this update on the computer where you sync apps, music, videos, and photos." [1]

[1] http://cache.gawkerassets.com/assets/images/lifehacker/2011/...

However, doesn't his expectation sound reasonable (especially for the "it just works" company)? And isn't the mismatch between expectations and reality one of his points?

We really don't know what happened between when his 87 year old grandfather walked into the Apple store and when he walked out with a restored machine. I can think of a lot of ways this ends up "just not working". Maybe grandpa used the word "restore" at some point not aware of it's specific meaning, heads were nodded and miscommunication happened.

Wife and I were planning to get her mother a tablet to video chat with before she passed unexpectedly a year ago. Had we done so and had we been in a similar situation I doubt I would have sent her to the Apple store with only the words "icloud backup" scrawled on a piece of paper. I mean it's total speculation but I think I would have had an email explaining exactly what to do or told her to wait until we were there to handle it.

Update, restore, "are you sure you want to do this?", "pick the right destination", etc are user unfriendly concepts, and will make people nervous. Auto-update apps, but let people undo. Make restores undoable. Change "are you really sure?" to "don't worry, you can always undo".

Of course, you could argue, this will waste storage space. Well, with a good diff algorithm to rely on, not really that much. And even if so, you can always merge older states together (e.g. the detail of change is mostly relevant to very recent events - a few weeks back, I only care about major things like when I deleted all my contacts and didn't realize until now).

- A lot of apps and iOS features sync with the network. Will need a little work to make sure a restored local state doesn't interfere with the network state. It's solvable.

The iPad had an iCloud account set up. It was unrelated to the current device's owner, so I couldn't back the device up to that account. There is a 'Remove account' button, but what's going to happen when I remove the account? Is something going to disappear from the iPad? How am I going to know?

I figured I should back up to the Mac first, then switch to the new iCloud account and restore if anything happened. I didn't even do that, because the last backup of contacts from the iPad got lost (probably because there was another iPad sync'ed with the same Mac) and I wasn't sure what would happen when I sync'ed it this time.

Maybe technical users tend to overthink these things, but data loss does happen and the current Mac's ecosystem is indeed confusing in that regard.

Turning syncing off warns that data will be lost (huh? I don't want you to delete anything, just stop syncing the two data sets).

Tis all a muddle.

And then backup. You have to choose between backing up to this computer and backing up to iCloud? Why? I certainly don't trust iCloud with my only backup, but having it as a remote adjunct would be handy. Why can't I back up to both?

It's horrible.

It's not perfect, but it works really well for me. Daily automated backups to the cloud + backups on my computer whenever I update the OS or upgrade devices.

I went through a horror scenario that scared me when I bought a new iPhone and my old pictures and videos for some reason did not sync over to the new device. I thought for a few brief moments that I lost 2 years worth of pictures and videos and that was enough to scar me permanently.

I now periodically back up all my pictures/videos from my iPhone and iPad to a folder in my Dropbox. Seeing all the files listed out in my folders gives me comfort, because I know there's no attempts at cleverness going haywire in the background, erasing and moving things around when I click "yes" or "no" to some popup question that I don't fully understand.

So I'm not sure what the right answer is. Sometimes I wish it wasn't as much magical as completely transparent about what's happening. Maybe there could be some nice UI that shows exactly what is stored, and people could somehow drag and drop data between devices?

I think in this sync issue DRM is at fault. Sync between old iPods and iTunes worked that way because music was DRM'ed and they didn't want you to give your friend your 40GB iPod and let him copy all your music. It has been carried away too long, there should be two way sync.

This is a special pain in the ass when you have more than one Mac.

Maybe I'm being paranoid but all I want is a perfect and completely transparent guarantee that I have a complete snapshot of my most important files. I'm willing to do the little manual work for it.

The product manager comes to me and says "I need you to add this field to the set of data stored for this thing". In the specific scenario I'm talking about, there's two ways it can go:

1. I blindly add the field for them. Later on, it turns out this field duplicates another field in that it can be calculated from that one. The fact that there's two fields that have the same "data" means that users get confused.

2. I ask the product manager what it is they're trying to accomplish by adding the field, so that I can make sure the implementation being asked for is the correct one. We find out it isn't and, instead of adding the field, we add an additional view of the data that allows the user to specify it two different ways. Everyone is happy.

My point is that the person going into the Apple store should make sure to describe what it is they are trying to accomplish, not just what they want the person to do. Similarly, the Apple worker should know to ask for what the person is trying to accomplish rather than implementing it. Both individuals could have done things better, both are responsible.

The issue is moot now that you can back your phone up to iCloud completely avoiding the iTunes step. It's slow and could be costly if you have a lot to backup, but at least it moves things in the right direction overall.

iPads have physical state: shattered, powered, glitchiness, temperature, cover, location they're in, way in which they're being held, etc...

iPads have hardware state: processor, CPU, RAM, GPU, storage available, etc

iPads have software state: booted, OS version, OS mode, current app, volume, what the app is doing...

iPads have user-state state: songs, contacts, high scores, the way the apps are laid out, pictures, videos, other pictures, other videos, FACEBOOK, emails, signatures...

We know all of these things. An iPad is a small flat touchscreen PC with some prissy software and expensive accessories and most anyone in the tech involved world can distinguish between all of these layers and figure out what's wrong when something's wrong.

For the tech uninvolved, there's no real distinction between any these states. The iPad is. The iPad is, for lack of a better word, an appliance. It is a thing they bought to do iPad.

“Hey Marco, I had the iCloud put on my iPad. Now I can’t even do anything with it."

It is no longer an iPad. The user-state-state is gone because of a misunderstanding and there's nothing that can be done to retrieve it. The user doesn't care how, why, whatever. iPad is not working.

What Apple is doing with iCloud is removing maintenance and reducing the chances of catastrophic loss of user-state-state. They are further ahead than basically anyone at this point, and had iCloud been running on the iPad in the story, it would have been near impossible for that iPad to become a non-working iPad. It backs up all of these things:

( Purchased music, movies, TV shows, apps, and books Photos and video in the Camera Roll Device settings App data Home screen and app organization Messages (iMessage, SMS, and MMS) Ringtones )

and quite a few more datatypes they don't advertise in a strong legal construct that allows Apple unbelievable flexibility and ability to make products that do things as expected. It is egregiously hard to delete an iCloud, even if you try.

State is a service. SIAS. State As A Service. Make whatever acronym you want.

People expect that when they get a new notepad their old notes will still be there.

We definitely have a long way to go, although I think a lot of the stuff we put up with is also due to accommodating external forces like backwards compatibility, pressure from the music and movie industries, etc.

Generational issues will decay over time as the population becomes made up of a greater proportion of 'digital natives', but the gap between rich and poor will still exist. We should take the lessons we learn here and try to apply them there when the time comes.

And it is not that he's not a sharp cookie anymore. He runs the household, still consults on his civil engineering projects, tinkers frequently with various things electronic/electrical, but GUIs stump him and his predicament has only gotten worse with the newer iterations of operating systems. For my generation, who grew up with the modern computing paradigms, this is unfathomable, but it is a real problem too, one with no real solution.

I have found my eventual solution in doing Teamviewer sessions for most problems. It is heartbreaking to make aged parents feel incompetent because they can't seem to grasp easily the same concepts we can grasp without even half a thought.

It was a little off-topic, but I just thought sharing that little story with others might be beneficial. I searched a lot before doing that but couldn't reliably verify I can move my Synced data between multiple installations, so maybe others in the same situation find it useful.

Expecting that something is easy and always works is not that helpful, and to some extend removes responsability from the consumer (which is great for the consumer in the short run).

It doesn't help that we (techies and others) use catchy phrases such as "It's easy" to convince people to give it a try. Because, for some, it will be difficult.

When you tell older generations about something "new" (email, smartphone, tablet, whichever) and they're hesitant or slightly sceptical, it's easy to hear yourself giving the argument: "But it's easy, you just have to...".

Don't say "but it's easy" in cases where you should've said "but it's easy for me".

Should the iPad experience be better? Sure, and I'd love to see them continue to strive towards it. My point is the other end of the equation: the consumers.

I think we need some rethinking into the whole mess of sync. It is not easier, even for some technically minded individuals.

And may be someday Apple could charge $50 or more per iDevices and have iCloud Backup as standard. No more messing around with iTunes Sync. And my friends wont cry when her iPhone has been stolen and lost all the pucs she took over the years.