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Moving to a New Mac: Lessons Learned

Recently, I helped a semi-retired friend (let’s call him Ishmael) replace his old Mac, a dual-processor Power Mac G4 running Mac OS X 10.4 Tiger. This friend is by no means a dummy — in fact, he’s a highly regarded professional in the entertainment industry — but he’s been too busy pursuing his craft to learn much computer lore. He can use a computer, of course, for basic stuff, like email and word processing, and even for some pretty advanced stuff, like high-end video editing, but when it comes to connecting and setting up a new computer, no: he has people to do that. People like me.

So one day Ishmael and I went to the local Apple Store to look at what he might want to purchase. We decided that a top-of-the-line 27-inch iMac would meet his needs. We also decided that Apple’s One-to-One service would be a good way to go, since it promised to migrate all of his data from the old machine to the new one, and would provide some training as well, to help Ishmael wrap his head around the differences between 10.4 Tiger and 10.7 Lion.

With that decided, a few days later I went to Ishmael’s house to disconnect his old machine and take both it and him to the Apple Store. So far so good.

Once in the store it only took a few minutes to find someone to help us and within half an hour we had purchased the new top-end iMac, a trackpad, AppleCare, and the One-to-One service. That’s when the “fun” started.

For Want of a Password -- The Apple Store employee with whom we were working attempted to enroll Ishmael in One-to-One service, but that service requires an Apple ID. Ishmael did not have an Apple ID — he’s never used iTunes or anything else that required it. So the Apple Store employee tried to create one for him. In attempting to create the Apple ID, however, the employee ran into a snag. For some reason the Apple ID enrollment didn’t seem to take, and he surmised that perhaps we needed to check Ishmael’s email to respond to a verification message from Apple.

The second snag: Ishmael did not know his email password. Now don’t laugh: he hasn’t had to enter the email password since the day, years ago, when someone helped him set up his email account. He simply has never needed it: In all that time, his email software had been sending it automatically every time he checked his mail.

So, accessing Ishmael’s webmail provider from one of the Macs in the Apple Store, we clicked the “Forgot password” link. The third snag: in order to reset Ishmael’s password, we needed to respond to an email sent from the ISP to the email account.

This was a real Catch-22 and a case study in security stupidity: to reset a forgotten password from the ISP, we needed that very same forgotten password in order to access Ishmael’s email account to get the email with the new password in it. But if we had known the old password, we wouldn’t have needed to change it in the first place. We could have easily found the old password, of course, via Keychain Access — that is, if we hadn’t disconnected his old Mac and toted it to the Apple Store, where they were working on it in a back room where customers weren’t allowed (and there were neither appropriate monitors nor space to work out in front, where we could have helped).

Fortunately, I had my iPhone. Unfortunately, the noise level in an Apple Store is just slightly lower than that of a Boeing 767, so trying to navigate the ISP’s phone tree and then explain the issue was almost impossible. Eventually, after 20 minutes of shouted phone discussion, the ISP said that we would need to call back from Ishmael’s home phone so they could verify his identity via caller ID.

Fourth snag: the Apple Store could not let us leave the machines at the store while we drove back to Ishmael’s home, so we had to load both the old machine and Ishmael’s new iMac into the car before we could go back to Ishmael’s house.

Once at Ishmael’s house, we left the computers in the car, called the ISP back, and after a very amusing-in-retrospect sequence of transferred calls and unintentional disconnections, we eventually made contact with the right person, had the email password reset, and hopped back into the car to drive back to the Apple Store, where we unloaded Ishmael’s old and new computers and once more attempted to finish the One-to-One process.

Upon trying to create an Apple ID again, we discovered that the original Apple ID creation attempt had, in fact, worked. This was yet another snag: our second Apple ID creation attempt failed because there was already an existing Apple ID associated with Ishmael’s email address. This time, though, the Apple Store employee helping us was able to work around the problem easily, get the Apple ID set up properly, and finish the One-to-One enrollment.

Then the Apple Store employee returned to the back room to make sure that the old Power Mac G4 was capable of having its data migrated. Another snag: she needed the login password. Ishmael did not know that one either; he’d never had to use it in all the time since the machine had originally been set up! The Apple Store employee was nonplussed but said she would see what she could do.

After a few minutes she came back and told us that the Power Mac G4 had never had a password: it had been set up so Ishmael could log in and respond to all password requests from Mac OS X by simply hitting Return at the password prompt! (Yes, I know, this was a major security lapse, although, given that Ishmael’s machine resided in his home office behind a locked door, and the home itself was protected by a security system, the vulnerability was not quite as bad as it might have been. Still, it’s not how I would have set it up.)

Finally, everything seemingly was in order and we left the Power Mac G4 and the new iMac at the store so the technical staff could put the machines in their queue to do the migration.

The Value of a Good Backup -- Alas, the sailing was still not destined to be smooth. A day or two later, the Apple Store called Ishmael to tell him that they had run into trouble migrating his data.

He and I went back to the store that evening to find out what the problem was. We were told that the Migration Assistant was unable to connect via FireWire, nor would it connect with Ethernet, nor with any other method. They said the Power Mac G4 seemed “deaf” to all attempts to communicate. This was odd, because it was both connecting to his external FireWire drives and using an Ethernet connection to his DSL modem before we took it to the store.

On the other hand, I also recalled my own struggles using the Migration Assistant with a new iMac that I had purchased for myself a month or two earlier: Migration Assistant was unable to maintain a connection with my 2006 Core Duo iMac with FireWire, nor could it do so with Ethernet. I eventually accomplished my migration using a Wi-Fi connection. It may be that the Migration Assistant has certain connectivity issues when running on the new iMacs. Whatever was actually the case, I suspected something else was the problem.

I asked the Apple Store technician if they had tried to make a disk image and migrate from that, but he told us that Apple’s policy was never to copy a user’s data to an external device. So, strike three and the Apple Store was out: we brought both machines back to Ishmael’s home and I agreed to come back the next day and try to see what could be done.

Luck was finally with us. Ishmael happened to have a couple of extra terabyte drives on hand, which he had used for various video projects. One of the drives had ample free space for me to make a disk image of his Power Mac G4’s system volume, so I did just that, using Carbon Copy Cloner, as I had learned from Joe Kissell’s “Take Control of Mac OS X Backups.”

A Matter of Accounts -- With the clone image made, I unpacked the new iMac, set it up, attached the backup drive, and was almost ready to go. When I fired up the new iMac, however, I discovered that the Apple Store technicians had reached the point of setting up a user account for Ishmael on it, using the same account name as on his Power Mac G4. They even created it without a password, just like Ishmael’s original account was configured.

The account name was a problem: as Joe’s book points out, you can’t merge user accounts with Migration Assistant. I therefore created a new administrative account on the iMac (it’s always good to have two, anyway), logged in with that, deleted the original login account, and finally, at long last, was able to try the Migration Assistant again, migrating Ishmael’s data from the disk image to the new iMac.

And, glory be, it worked.

When the migration finished, I configured Ishmael’s migrated account to have a real password, and I made sure that he had a record of it stored in a safe place. I also showed him how to use Keychain Access to find out what his other passwords were. I then set his account to be the login account, cleaned up a few odds and ends, and went my merry way.

Lessons Learned -- There’s a lot that I learned from this adventure, but two points stand out.

First, keep track of your passwords. Even if Keychain Access (or whatever password utility you use) eliminates your having to type them yourself, you have to know what they are when all your fine technology is unavailable.

Second, always have a good backup on hand. If Ishmael had made a complete backup to begin with, we could have taken that to the Apple Store and had them migrate his data from it, thus avoiding our having to carry his old machine to the Apple Store — twice.

If there is a third lesson, it’s this: don’t panic. There’s almost always another way around a seemingly insurmountable problem. Stop, take a deep breath, and think. Reflection and research can usually get you out of most sticky situations.

Finally, I must point out that I can’t blame the Apple Store for any of our problems. The employees were unfailingly kind, helpful, and encouraging, and they went as far as they were allowed to go on our behalf. It was a combination of bad luck, inflexible policies, and poor planning that led to our problems. I can’t do anything about luck or Apple’s in-store policies, but I’ll plan things better the next time I find myself helping a friend move to a new machine.


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Comments about Moving to a New Mac: Lessons Learned
(Comments are closed.)

JohnB (SciFiOne)   2011-09-23 20:56
Fabulous, enjoyed every word.
Michelle Steiner  2011-09-23 21:40
Why would having taken the old iMac to the store prevented you from using keychain access?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2011-09-23 21:52
Because this was a tower Mac, with no monitor, keyboard or mouse: all that the Apple Store wanted us to bring in was the tower itself. In addition, once we arrived the tower was stored in the back room of the Apple Store, where customers are not allowed to go (for various legitimate liability reasons). In short, we could not get to the machine to explore its contents.
David Vereschagin  2011-09-24 01:02
I'm still not getting this: You were in an Apple Store. They have monitors and keyboards and mice. Were the staff really being that obtuse?
Michael E. Cohen  An apple icon for a TidBITS Staffer 2011-09-24 01:25
Sure they had monitors: but not for a six-year old G4 Powermac, which has an entirely different video connector interface than the current product line. No doubt they had a monitor of that sort in the back room, but customers are not allowed to go into that room (for good legal reasons). The staff were not being obtuse at all: they did everything they could reasonably be expected to do within Apple's policy guidelines.

Don't forget, in the customer area of an Apple Store, there is no space to set up a customer's machine and diagnose it other than at the Genius Bar. The Genius Bar was completely busy with customers who had made reservations in advance. I was not about to bully my way into the Genius Bar line and demand that the techs haul a compatible monitor out of their tech service area because I had not thought to find out the password ahead of time. That would have been wrong and rude.
MikeIT  2011-09-27 21:46
That is rubbish! If they were really helpful they would use an adapter that they surely have somewhere on a
shelf and quickly hook it up to one of their showroom screens. Anyway... Have they refunded you for One-On-One service which in fact didn't work out?
Also if you were able to do all that migration yourself in the end why would didn't you try it in the first place? Have a little faith! : )
Got to love how the big companies deal with a customer... Next time do yourself a favour find a local, small IT company that would do a better job saving you all that hassle!
MACMAD  2011-09-24 11:26
Been there done that. I cannot remember how many times I offered to oversee someone purchasing a mac and it ended up costing me many hours, if not days of time.
The real kicker of it all is when they finally set down and log into their system for the first time, they sigh, half turn to you and mumble thanks, makes it all worthwhile. I still can't figure out why, but it just does.
Howard  2011-09-25 19:04
Been in a similar place with friends.

a) People who fail to listen to years and years of advice to keep note of passwords and keep backups are a pain in the butt.

b) Regarding the email problem - I find it odd that a new Gmail or hotmail account wasn't just setup on the fly ... but maybe I missed something.

Well done to stay calm and sort it all out !
Meggeler  2011-09-26 00:24
Being an old man I understand. I, bring a "monday morning quarterback" See what was wrong, with the 'system'. Lot of difference if you on the front line. Thanks for the advice or warning :)\
Michael  2011-09-26 22:48
Great story! At least you didn't end up in Mexico like Michael Douglas in The Game with no (computer) identity at all...
julieg  2011-09-27 01:31
There would be a problem with a Time Machine backup on a 10.4 box and that is that Time Machine came with 10.5. Great Article anyway!
Adam Engst  An apple icon for a TidBITS Staffer 2011-09-27 12:30
Doh! That's my fault - I was trying to expand out the suggestion of the backup during last-minute editing and totally blanked on the fact that Time Machine hadn't been around then. I'll delete it.
werkingman  2011-09-27 03:37
Excellent read, I enjoyed every word. Been there done that too.
Regarding your second point, lessons learned, bring backups on hard drive with you for the data transfer if all else fails- Unfortunately Apple will not accept a hard drive for data transfers, apparently, it's a one to one policy for data transfers to go from one computer to another computer only.
Graham Allsopp  2011-09-27 08:53
Hmmm... This is definitely one aspect I'm nervous of in the transition to iCloud.
Syncing all my Keychains with MobileMe means it's a painless operation to retrieve any password. Once they're out of sync, you know the one password you want to retrieve will be the one that's out of sync.
werkingman  2011-09-27 11:58
The transition will exclude those mobile me members who like me, who have not or are not able to upgrade to lion. Bah humbug to the loss of mobile me! Sometimes Apple seems like such a fickle lover, giving me what i want for awhile, then taking away...i have to wait. What kind of fickle commitment has Apple to iCloud? 3 yrs, 5 yrs, 10 yrs?
Bob Bright  2011-09-27 12:21
Enjoyed reading this excellent saga! And I learned something too - didn't know it was possible (and easy, kinda scary) to access passwords through the Keychain Access.
Adam Engst  An apple icon for a TidBITS Staffer 2011-09-27 15:28
Yes, you really do want your keychain password to be something fairly strong because of that.
Craig Luis  2011-09-27 22:38
Ah yes, the old G4 tower. We have had quite a number of them that refused to be recognized for migration just like your experience ("deaf" to all attempts to communicate). But having a good shop, we just pull the hard drive and attach it with an external dock to the new machine. Great to see this in writing.
Jean-Pierre Fritz  2011-12-20 12:33
Thanks for the article, I was hoping someone would write about my migration experiences so, here is a suggestion for another migration article. Last august, 2010, I decide to splurge and buy a 27" iMac with a 256gb SSD and 1tb internal drive. Prior to that I had an iMac with a 750gb internal drive. I also had a Time Machine backup. So, the challenge here is to try and fit a 750gb Time Machine backup on a 256gb SSD using Migration Assistant. Yes, you absolutely want to use the SSD as the boot drive. Have fun...
Adam Engst  An apple icon for a TidBITS Staffer 2011-12-20 12:59
Yes, that would be a bit tricky. I'd probably use Migration Assistant to move the /Users folders, if they'd fit, along with settings. And if they didn't fit, the problems would likely be in ~/Pictures and ~/Movies, so hopefully it would be fairly easy to move the really large things off to another drive before migrating.
Jean-Pierre Fritz  2011-12-21 11:18
I also came across the username problem from Time Machine. I did end up copying different folders selectively but, the selection windows in Migration Assistant is pretty useless because you can't stretch it, I had to take screen capture to figure out what I had selected. If apple offers a computer with 2 internal storage devices, it should update Migration Assistant accordingly, seriously, it's been over a year.