Apple Jam

Posted on Tuesday, September 25, 2018

I was going write about something else but having just spent many stress-filled hours trying to upgrade my Apple devices to iOS 12, I thought I should share my experiences.

Full disclosure: with the exception of the bottleneck I describe below, the upgrade of my iPhone worked perfectly. It is my iPad Air 2 that was the problem and there were ‘mitigating circumstances’ any one of which MAY repeat MAY might be root cause. More later.

The bottleneck with the iPhone was that, in keeping with what I had always understood was ‘best practice’ for a major upgrade (in this case to 12), I connected my phone to iTunes on my laptop and tried to save a security copy.

Except my very sexy Hewlett-Packard Spectre has a solid-state drive and when I bought it three years ago the drive was a mere 250GB. (Cue the Monty Python ‘Luxury!’ sketch.)


That does not turn out to be very much space – especially when iCloud is enabled and so all of your photos and all of the photos people send on WhatsApp – are being backed up to your hard-drive. Twice in my case. Don’t ask.

Not only did I have to copy all of this material to an outboard hard-drive to get rid of it, but I could not do it all at once because, again, I lacked the hard-drive space on the laptop to do so.

It took several hours of moving things a bit at a time and then deleting them before I finally got enough free space to finish the rest of the job overnight.

The next morning, upgrading my iPhone was easy.

So then I turned to my iPad which, of course, had the same problem or worse: not enough space for a full, local security copy. However, there was an iCloud ‘critical parameters’ security copy from the morning before and the iPhone upgrade had worked like a charm, so I cheerfully started the upgrade.

(Later, I discovered that my disk-space was being consumed with iOS security copies! There were four or five buried down in the depths of the Roaming folder, consuming well over 100GB, half my storage. It took a Google search and some useful software called WinDirStat to find this out and deal with it. From now on, I will only use the iCloud critical parameters backup and live with the few hours necessary to restore any software from the App Store. It is an opportunity to purge stuff that I no longer use. Again, for my thesis, is this something the average user would be able to do? Want to do?)

When it reached the point where it was about to restart, the dreaded “Please connect to iTunes” picture appeared (which, of course, I already was). In iTunes there was a message that an ‘unknown error had occurred’.

I unplugged and re-plugged.


Tried that again.


I did a hard reset (hold Off and Home buttons simultaneously). That at least got the iPad to recognize that it was attached to iTunes. It offered to do an Upgrade. Failed. Try again. It offered to do a Restore.

Now we are getting somewhere I thought!



Then my iPad woke up and it appeared to be upgraded.

I was in the Select language/Sign into iCloud pages. It offered to do a Quick Start if I would only cozy my iPhone up to my iPad.

They recognized each other! The iPad started restoring!

Then it failed.

Unknown error. “Connect to iTunes”. Which, of course, I was (again).

I did a hard reset again and this time I again got the upgrade dialogue but it skipped the ‘cozy up your iPhone’ step and I could enter my Apple ID.

That got me to an iCloud restore dialogue and now everything is being loaded (Apps, iCloud photos, Mail, Calendar etc.). I do not know if I have lost anything permanently – or at least anything that I care about – but that will have to wait until everything finishes updating. (Later: All good.) So far the only thing missing seems to be Touch-ID, which is easy to reestablish.

Before I start my harangue, you might want to scroll down to the end and read the mitigating circumstances. Some of you may roll your eyes and say “Of course, you had problems!”. Others may agree with me that these are (potential) reasons but not excuses.

I remember reading last year sometime that Apple wanted to simplify its upgrade procedures. It would be hard for anyone from Cupertino to admit that Redmond bettered them on anything, but operating systems upgrades are one thing, apparently.

Windows upgrades happen all the time. You only notice if you shut down your computer and are told there is an upgrade waiting or you open the lid and find it has restarted by itself. The last major upgrade, to Windows 10, was more complicated but still painless from a user perspective. It took time, but you did not really have to do anything, no data was lost, and everything worked like a charm afterward.

Compare this experience to what I just described.

Admittedly, I do not have a Mac and perhaps with the proper ‘big brother machine’ things work as easily as Windows. Common DNA and all that. Conversely, I do not have a Windows Mobile phone (who does?) and so maybe on the Microsoft ‘small screen’ the experience is not so pleasant as on the ‘big screen’.

However, I suspect that the comment I read about Apple wanting to emulate Microsoft’s success with upgrades suggests that things are not so great in the Mac world nor so bad in Windows Mobile.

What do unsophisticated iOS users do when it comes time to upgrade?

What does my 92-year old mother do with her iPad? What do people who do not have PCs / Macs do (like my sister-in-law)?

If I had just said “Update” and my iPad had replied “Update when connected to energy and WiFi” (I forget the exact phrase) would everything have gone better? Better than doing what I was told I was supposed to do: save a security copy, transfer my purchases to iTunes and do the update connected to iTunes on my PC?

Do the unsophisticated users wind up better off because they are unaware that glitches can happen in iOS upgrades?

Or do they take it to their Apple Store (or equivalent) for help? Or equivalently, to the closest teenager? (Who probably does not have a PC so what do they do?)

Or do they just not bother to upgrade? (Like my mother who is partially blind and so cannot see the messages.)

My guess is that a lot upgrade without connecting to iTunes and if there is a failure, like I had, they take their ‘bricked’ iPhone to their local Apple Store.

Another significant percentage – maybe the majority – do not bother to upgrade at all. Because I had not upgraded for a couple of years before iOS 12 (see below), I can assure you the consequences are minimal. I had started to find software incompatibilities and that was part of my motivation to change. Staring at the very expensive paperweight that my iPad had just become, I seriously questioned my decision to do the upgrade.

I do not know what happens with Android, how easy it is to upgrade or what the consequences of not upgrading might be.

But I think Apple has to get its act together and vastly simplify the update procedure. Most things on iOS are just ‘plug-and-play’. Why is an operating system upgrade so fraught with peril?

If smart devices like larger screen smartphones are going to displace PCs for everyone but business users, the iOS upgrade procedure has to work infinitely better, on a standalone basis, than it does today.

Mitigating circumstances or why this might not be entirely Apple’s fault

If I were in Apple I would blame me for not having done the backup but see my harangue for why I do not consider that a legitimate argument.

I admit that I was leaping from 10.3.3 to 12. iOS 11 had a number of bugs and I kept reading that I should wait. Somewhere around 11.4 or 11.5 these disappeared but the pain of doing a full backup etc. meant I never got around to it. There was always something more urgent or more fun to do on a Saturday morning which is when I normally do full connect-to-iTunes upgrades.

I still do not think this is very ‘user friendly’ although Microsoft does not let you upgrade to Windows 10 from Windows 7 without efort. Actually, the Windows upgrade itself is not that painful, especially to Windows 10. The pain is only that you cannot now do it for free. There was a time when it was free (from Windows 7 to Windows 8 and then from 8 to 10) and if you missed that, too bad. You have to pay. But the actual upgrade is simple and does not require a full backup of your hard-disk.

The second mitigating circumstance was that my iPad has a SIM-card but I recently cancelled the service. I had never got it to work (and yes, after the first few attempts, I gave up trying to see why) so I decided it made no sense to keep paying. At one point in the cycle of hard resets, iTunes suggested I make sure the SIM-card was well seated and enter the PIN if required. I did another reset and the message never repeated but it did make me wonder if that was part of the problem.

Finally – and this is the only reason I can accept is truly ‘mine’ – it appears that my Internet failed just at the time that the software load completed. I think that iTunes or the iPad were checking with Apple right at that moment to authorize the activation of the software and that may be the cause of the original hiccup. However, I only figured this out by carefully reading a rather confusing iTunes error message that said something about not being able to reach the server, and then seeing that I was not connected to WiFi.

I have no idea what happens to a Windows upgrade if the Internet goes down in the middle. It may not be pretty but then, given Windows’ need to deal with a variety of enterprise customers in a variety of circumstances it could very well be graceful. Microsoft tells you not to turn off your computer in the middle of an upgrade so ‘graceful’ no doubt has its limits.

It is not surprising that an internet failure at a key point is going to cause the whole process to fail. But restarting the process for a consumer device should be much more graceful than was my experience.

I still think the error messages were confusing and so, to return to my thesis, the average user would not have got through to the end of this. They probably would have gone to a technician to help them with their bricked iPad.

Or not bothered in the first place.

(Title reference: The play on words originally belongs to George Harrison, the title of the third disc from his great three-album set All Things Must Pass. It was all informal improvisations – jams – recorded in Apple Studios.)


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