This article originally appeared in TidBITS on 2015-08-27 at 1:54 p.m.
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Migrating to a New Mac in the Real World

by Michael E. Cohen

It all began earlier this month with a soft, extremely high-pitched intermittent whine from the upper-right corner of my mid-2011 iMac. Then, a few evenings ago, I heard about a dozen clicks and my Mac shut down. I couldn’t get it to reboot normally, from a safe boot (hold down Shift at the startup chime), nor even from a recovery boot (hold down Command-R). An Internet recovery boot (hold down Command-Option-R) did work, but its included Disk Utility app had a grim tale to tell: my Mac’s internal drive could not be found.

A trip to my local Apple Store Genius Bar confirmed that the Mac’s drive had rung down the curtain and was now an ex-drive. Although the Apple Genius told me they could install a new drive, it would take a week, and since I had been planning to buy a new iMac next year, I decided I’d just push that purchase forward a few months (besides, I can always connect an external drive to the old iMac and use it as a test machine). So I packed up my old iMac, took out a credit card, and within minutes walked out of the Apple Store with both my old iMac and a new iMac with 5K Retina display. I drove home, anxious to discover whether Time Machine really would do what it was supposed to do. Would it “just work”?

The answer is “more or less”; I did get all of my backed-up files restored, and most of my settings as well, but there were more than a few loose ends and hiccups along the way.

I strongly suspect that my experiences restoring my Mac’s contents to a new Mac from Time Machine are similar to those of other users who have had to do the same thing. I present the following tale for those of you who haven’t (yet) had that experience: what I encountered may help prepare you for what could lie ahead.

The Time Capsule Migration -- My Time Machine backup resides in a 2 TB Time Capsule that sits near my desk. Pack-rat that I am, I keep an Ethernet cable in my Cupboard of Arcane Connectors: I strung that between my new iMac and the Time Capsule before I started the migration. I could have used the Time Capsule’s Wi-Fi connection instead, but restoring a backup that way would have taken considerably more time — the last time I did a migration over Wi-Fi, it consumed a full weekend. Crossing my fingers, I booted my new iMac for the first time. It was 7:20 PM on a Saturday evening.

Upon starting up, my new iMac recognized the Time Capsule and offered me the opportunity to set it up from a Time Machine backup. I chose that option and we were off to the races… though, as races go, it was a marathon, not a sprint.

The first obstacle was the appearance of a dialog that told me the Mac was “preparing” to transfer my backup: it had no progress indicator and, as minute after minute passed, it gave no impression that any progress actually was being made. In my younger, more impatient days, I would have forced a reboot and tried again, but that night I told myself to wait an hour before giving up. After “only” 30 minutes, though, the “preparing” dialog was replaced by one with a progress gauge, and, what’s more, a time estimate! It told of 6 hours remaining — that estimate quickly became more than 8 hours, then fell to 7, then to 4, then to 3.5 before stabilizing at 5 hours. Files and settings began transferring and I walked away.

I checked in an hour later and saw the estimated time to completion was now 36 hours! As I watched, it jumped to 40, and soon got as high as 72 hours. I resolved not to panic and walked away. A few fretful minutes later I came back for another look and relievedly saw that the estimated time remaining in the migration was once again under 5 hours.

In fact, the data migration from my Time Capsule to my iMac via Ethernet, involving some 300 GB of data, took just under 6 hours: close to the original estimate!

The moral of this episode: patience is a virtue. Progress gauges are notorious liars, so don’t hasten to pull the plug if you worry things are hung up, and don’t be disheartened by interim time estimates that may be wildly incorrect.

Back to My Desktops -- With the data migration completed, my new iMac asked me some of the usual new Mac questions (pick a time zone, choose a language), and then it rebooted and asked me to log in to one of my migrated user accounts (they all seemed to have transferred). It was now well after midnight, but I couldn’t go to bed without seeing if my old familiar desktops were truly back in my main user account (I use Mission Control and have seven desktops that I move between). They were.

But I couldn’t move among them with a flick of my fingers as I was accustomed to because the new iMac, which came with a Magic Mouse, didn’t recognize my trackpad: the Bluetooth setting for the trackpad didn’t migrate so I had to pair my trackpad manually with the new machine. Not surprising, really: the trackpad itself knew that it was paired already with a different device than my new iMac, but with the help of the Bluetooth pane of System Preferences I soon got the two talking.

Before I could even get to that, though, I had to deal with a flurry of requests for my iCloud password. Dialog after dialog came up requesting it, four or five in a row. This flurry was finally followed by an alert telling me that some of my apps required app-specific passwords, and the alert offered to help me create them. The alert didn’t tell me which apps needed those passwords, but I noticed that it sported a Messages icon.

The light eventually dawned: a few months ago I had enabled two-step authentication for my Apple ID [1], which required me to create an app-specific password [2] to be used by both FaceTime and Messages (why any of Apple’s own apps require this is another question). It occurred to me that the flurry of iCloud password requests might really be very poorly worded requests for the app-specific FaceTime/Messages password. Fortunately, I had that app-specific password stored in 1Password [3] and could retrieve it with the 1Password app on my iPad. So I cancelled the alert, and, on the next iCloud password request, I fed it the FaceTime/Messages app-specific password. The flurry stopped.

It was now heading toward 1 AM, but before I went to bed I wanted to make sure that my email had survived the migration. When I opened Mail, though, I saw a dialog telling me that Mail would have to process all my saved messages, several hundreds of thousands of them, a process that would take at least another hour. I decided to let Mail have its way and toddled off to bed. After a few hours of restless sleep, I returned to my new iMac and saw that, indeed, all of my mail was in place. What’s more, Mail had found a couple of messages that had gotten lost in its bowels on my old Mac last year and had never been sent; while I was sleeping Mail sent them for me, no doubt confusing the recipients.

Happily, I found that the migration had preserved all my mail accounts — one account seemed to have had its settings mangled, but it turned out later that the problem was actually at the mail server: the settings were intact.

Next, I wanted to see if my Photos library had also made the leap to my new machine. When I went to the Dock to launch Photos, however, there was a great big question mark where the Photos icon should have been! It turns out that the version of Yosemite on my new iMac was the one that came out prior to the release of Photos. Although Time Machine had backed up my old Mac’s system along with the rest of my data, the migration did not replace the installed version of the operating system or any Apple apps on my new iMac. So it was off to the Mac App Store to upgrade Yosemite. When the upgrade to OS X 10.10.5 was complete, Photos was back on my Dock, and my Photos library was accessible once more — and it was intact.

Finally, I got a prompt asking me if I wanted my Time Machine to “adopt” the previous backup for my new machine, warning me that if I chose to do so, I wouldn’t be able to use it again with my old Mac. I chose to do so, which means I can seamlessly use Time Machine to retrieve files from before the crash as well as after: as far as Time Machine is concerned, my new Mac and my old Mac are the same Mac.

The moral of this episode: Be prepared for the unexpected. You will still have a lot of things left to set up, and updates to install, when you migrate from a Time Machine backup to a new Mac. Furthermore, Migration Assistant may say that it is transferring your settings, but it doesn’t transfer all of them. If you haven’t saved the passwords for your Mac’s services and accounts somewhere that you can get to as needed, do it. Do it right now.

Loose Ends and Hiccups -- Even after my new iMac was finally set up, there were still a few problems that I had to resolve.

One of them was the matter of third-party software licenses. Some survived the migration intact, while others, such as for Smile’s PDFpen and TextExpander, and for my copy of Microsoft Office 2011, did not. Smile has a lookup service [4] that allows you to retrieve purchased license keys, but for the Microsoft Office key, you may need to make a phone call [5]. Fortunately, I had my Office key squirreled away in 1Password. Unfortunately, Smile’s lookup service didn’t work for me because I had received my keys directly from Smile when I was writing “Take Control of PDFpen 7” and “Take Control of TextExpander [7],” but since the good folks at Smile know me, I was able to resolve that problem with a quick email. (Note: In case you are wondering, yes, the Smile licenses are now in my 1Password archive.)

I had one other TextExpander problem: all my snippets were missing! It turns out that was because I have them stored in Dropbox, and because my Dropbox settings didn’t transfer for some reason, they were inaccessible to TextExpander. Once I reauthorized my Dropbox account for my new iMac, I was able to relink TextExpander to its settings and my snippets came back.

But there was still one more Dropbox hiccup: none of my Dropbox notification settings made the migration, so once I authorized my new Mac to use Dropbox, I began seeing notifications every time someone changed something in one of my shared Dropbox folders (and, as a Take Control author/editor, I share a lot of Dropbox folders with my colleagues). A quick trip to the Notifications pane of System Preferences cleared that up.

Then there was iTunes. When I opened it, I was warned that some of my media was inaccessible because my Mac was not authorized for my iTunes account (thank you, DRM!). What’s more, I had no more authorizations left: I had previously used all five that iTunes makes available. Fortunately, Apple does allow you, once each year, to deauthorize all the computers [8] authorized for a specific iTunes account. Since I couldn’t deauthorize my old Mac (no hard drive, remember), I deauthorized all the computers using my account, and then authorized my new one. My media was once again accessible.

I also encountered a weird Mail hiccup. For some reason, even though all of my mail had transferred, none of my smart mailboxes seemed to work, nor did any new ones that I created. It turns out that Spotlight was the culprit: even though Mail had processed all my migrated mail, for some reason Spotlight, upon which smart mailboxes depend, hadn’t indexed that mail. The solution for this was simple: once I forced Spotlight to re-index my new iMac’s hard drive, the smart mailboxes began working again. (Though the process can take hours, reindexing a hard drive is easy: in the Privacy view of the Spotlight preference pane, add your hard drive to wipe its index, wait a few seconds, and then remove the drive.)

Finally, I found that I was no longer able to make phone calls from my Mac using my iPhone over Wi-Fi. Every time I enabled the iPhone Cellular Calls setting (which you can find in FaceTime’s preferences) it immediately disabled itself, with an alert telling me that my Mac and iPhone had to be using the same iCloud account. Frustratingly, they already were! Fixing this, though, turned out to be simple too: I logged my Mac out of my iCloud account, and then logged it back in. After that, the iPhone Cellular Calls setting worked.

The moral of this episode: It’s not over until it’s over. Even if you get your Mac successfully migrated, you will likely find a few things that need tweaking and readjusting in the days and weeks ahead.

Final Thoughts -- Few of us are lucky enough never to encounter the unexpected loss of a hard drive or even a Mac. Stuff inevitably happens. But if you have at least one good up-to-date backup, and if you keep track of all of your software licenses and service passwords, you can usually turn a disaster into nothing more than a time-consuming inconvenience.

Developing a backup strategy is not hard (read Joe Kissell’s “Backing Up Your Mac: A Joe On Tech Guide [9]”), and recording new logins and licenses may be a chore, but it takes only seconds for each one. Do these things, and if you ever find yourself standing in the smoking crater of what was once your Mac, you can climb out again, secure in the knowledge that your most irreplaceable stuff — the pictures, documents, mail, and media you have accumulated over the years — is intact.