Upgrading A Mac System, part 2: Migration

Photo credit: Derorgmas
Wikimedia Commons, CC BY-SA 4.0

The Upgrading A Mac System series:

• Part 1: Hardware Purchase
• Part 2: Migration
• Part 3: Apps
• Part 4: Peripheral Hardware

In part 1 of this article series, I explained why I needed to upgrade my old Mac, what I bought, and the shipping process.

Now that the computer had arrived, the next step was to move all of my data from the old computer to the new one. In the past, I did this the hard way - I manually created user accounts (an administrator, my personal account, and accounts for my wife and daughter). I then copied all of our documents over the LAN, manually installed all the software I require, ending up with a working system. The whole process usually takes a week or two, plus all the time needed to configure my preferences in everything.

This time, I decided to use Apple's Migration Assistant utility to speed up the process. This, as it turns out, was a mixed bag. Some parts of the migration worked flawlessly, and other parts made a mess I had to clean up after.

The easiest way to migrate a working system to a new system is to run the Migration Assistant application on the old computer and tell it you want to migrate its contents to a new computer. This shuts down macOS and boots it into a special mode where the Migration Assistant utility on the new computer can connect to it and start transferring everything.

Unfortunately, this doesn't work for servers. The Migration Assistant utility refused to come up on the old computer. It dutifully shut down macOS and rebooted into migration mode. Then it told me that I'm running a server and therefore can't migrate this way - I need to migrate from a backup disk. Then it rebooted back to the normal macOS desktop. Thanks, Apple. Couldn't you have told me this before I wasted a half hour shutting down and rebooting everything?

(Incidentally, I'm curious if Migration assistant noticed the fact that I had installed the macOS Server app or if it knows that this particular hardware configuration was sold as server equipment. Either way it sucks - can't Apple ask me if I'm willing to let the server be down for a day during migration?)

So I decided to try and migrate from one of my system backup clones. I have two full system clones on external hard drives. Since I didn't want to go and unpack all my adapter dongles right away, I figured I'd just connect the drive with a USB (2.0) cable. Migration Assistant found the drive and (seemingly) started the migration, so I left it to run. I came back an hour or two later to find that it barely made any progress and was going to require 40 more hours to complete.

WTF? I know USB 2.0 is slow, but it's not that slow. I canceled the migration. The Mac then decided to reboot itself instead of simply bringing me back to my set of migration options. I'm starting to get the feeling that Apple's famous UI experts didn't work on the Migration Assistant process.

After rebooting, this time I broke out the adapter dongles. First a Thunderbolt 3 to Thunderbolt 2 adapter. Then connect that to a Thunderbolt to FireWire adapter. Then connect that to my existing FireWire 800-to-400 adapter, and connect that to the FireWire 400 hub where my hard drives (and iSight camera) are all attached. A really long chain of adapters, but it worked flawlessly.

Using the adapter chain, this time I told Migration Assistant to migrate everything from my latest Time Machine backup, telling it to wipe and replace whatever had been copied during the prior migration attempt. It took a long time (about 14 hours), but it completed. I logged in to my administrator account in order to reset the passwords on all my other accounts and then went to log in to my own account, in order to find...

Nothing. I logged in, but it was like a new account. None of my documents, an empty Music library. Nothing. I looked at the rest of the system and found that everything in the Applications folder copied over just fine. So did my wife's and my daughter's home directories. But not mine.

So I fire up my copy of Carbon Copy Cloner (which worked great - the license key file migrated over just fine) and used it to clone my home directory from a backup drive to the new computer. Wait several more hours for it to complete.

When I come back (the next morning), I now have my home directory. I needed to manually copy a few other folders (including my Photos library) over from the backup of the older computer's second hard drive (since they were never in my home directory), and wait a few more hours, but I finally got everything where it belongs in my home directory.

So let's fire up Music and see if it migrated my iTunes library. Nope. An empty library. The iTunes library is present, but it's not being loaded. OK. Probably an artifact from logging in and running Music when the iTunes library was missing. Delete the Music library and try again. Still got a blank library. Fortunately, I remembered that you can manually load alternate libraries in Music (and iTunes before it). Delete the Music library again. Then launch Music while holding the Option key. I get a window asking me to select a library. I select my old iTunes library. After a short delay, it generates a Music library pointing to all my music. No data lost.

The only casualty there is that my view settings from iTunes were lost. I had to go back to every single one of my 43 playlists and set them to view "as Songs", turn on the columns I want to see, turn off the columns I don't want to see, and then reorder the columns. (For those who care, my columns, from left to right, are Title, Time, Artist, Year, Album by Artist/Year (sorted on this column), Disc #, Track #, Genre, BPM, Rating and Album Rating). I didn't bother changing them all right away, but did that later, when I had some free time to spare.

Next up, Photos. Same problem. There was a new Photos library and it didn't find mine. But the same trick that works for Music also works for Photos. Launch the app while holding Option and you get a list of available libraries, and a button where you can add new ones. So I added my old library and opened it.

The migration process was pretty slow, compared to Music. It took about 30 minutes for Photos to migrate the library to the new format. Then, although Photos was fully operational, it was building up some photo analysis databases in the background (to recognize faces, generate "curated" slide shows, etc.) Fortunately, that process truly is background, so I could work with Photos as it churned. I made the old library my official iCloud photo library and deleted the blank one that the system auto-created for me. I then left Photos running until processing finished (many hours later).

Microsoft Office's migration was surprisingly simple. I was already an Office 365 user, so all I had to do was launch each Office app (Word, Excel, PowerPoint, Outlook and OneNote). The first one asked me to log in to my Microsoft account, which I did. The others just worked afterward. Then I used the Microsoft Auto Update tool to upgrade all of them to the latest versions.

The only weird thing here was the fact that Auto Update would not attempt to upgrade an app until after I ran it once. Then it upgraded just fine. I assume this wouldn't have been necessary if I had instead downloaded a new installer from Microsoft's web site.

So, with my account finally working normally, I went over to my wife's account and my daughter's account. They migrated flawlessly. All the documents were there, launching Music auto-migrated their music libraries from iTunes and launching Photos auto-migrated their default Photos libraries. Photos migration still took a long time to complete, but nothing went wrong.

So there's the migration process I went through. In part 3, I'll talk about getting my applications up and running. What worked, what didn't work and some pleasant surprises.