When migrating to a new operating system, Look Before You Leap!

I can’t help it. As soon as I hear of a new version of anything, whether it’s an application or the entire operating system, I have to install it.

Now prudence would lead one to take careful steps and wait until all of the wrinkles are ironed out before starting. I was almost not prudent enough this week.

Mac OS X Snow Leopard

So folks have been talking about the new Snow Leopard operating system for Mac. Over the past year, Apple has been positioning this version as more of a “under the hood” upgrade that tightens things up rather than a glitzy overhaul of the user interface. No matter what they said it was, I figured that it was newer, and therefore better, than the current OS—Leopard–and I had to have it.

I ordered my copy last week on Amazon and sat down with a smile as I awaited its arrival. And then I thought about doing a few quick Googles to see how other people have been making out with Snow Leopard. I immediately happened upon a few upgrade guides like this one, providing sage advice about the upgrade process. They recommended the “slash and burn” method, starting from a clean hard drive, and I felt that was a good idea. Nothing better than a wipe and fresh install to make your machine zip along twice as fast. And therein lies a tale.

The first sign of trouble

As I was reading up on the Snow Leopard upgrade process, I happened upon lists of “unsupported software” and casually glanced at the lists, expecting esoteric tools only used by three über geeks in the audio recording industry or perhaps some exotic ray-tracing software. Much to my surprise, I saw two of my favorite applications, in a very very short list of troublesome apps: Parallels and EyeTV.

I immediately checked the versions and breathed a sigh of relief when I saw that my EyeTV version was safe. But, Parallels was another story… They have no plans for patching Parallels 3 to work with Snow Leopard, and why should they, when they can sell us Parallels 4!

So, I ordered my fresh copy of Parallels 4, from Amazon with a twenty dollar rebate. When it arrived, I spent an evening upgrading Parallels, and I thought I was all set for Snow Leopard.

Preventative Measures

Following the advice of the upgrade websites, and prior experience, I used Carbon Copy Cloner to make a full backup of my hard drive on a spare external drive. On a hunch, I turned on the drive that I use for Time Machine and had it do one final “Time Machine” sweep through the system before bidding adiu to Leopard.

I knew that I had all of my installation media for stuff like iLife and Photoshop Elements, and I had all of my license keys in electronic form. It would be a simple matter of mounting the backup drive, copying over my loads of documents, and peering into them to find keys.

The first attempt

I boldly inserted the Snow Leopard disk and booted from the DVD drive, selecting the “Slash and Burn” method of installation. I reformatted the hard drive and went off for dinner while Snow Leopard installed.

Trouble

When I got home that evening, I started the lengthy process of installing stuff. I suddenly realized that it was not as easy as I had hoped: it’s one thing to reinstall something like Microsoft Office, but there seemed to be more loose ends than I had considered:

• How would I migrate my Mail settings from the old image to the new?
• What was the best way to migrate the Address Book contents?
• iTunes is great, but it has tendrils in everything. Can I simply copy my old library to the new without messing up my iPhone, Address Book, or other linked stuff?
• How about those nice password tools such as 1Password and SplashID that keep your passwords safe and sound? I had no clue how to get their contents from the backup. I wasn’t sure if it was even possible to do so—perhaps I was supposed to have exported the data beforehand.

It was becoming clearer to me that I had not done my homework at all.

More trouble

My initial shock at the depth of the upgrade process led me to start making a list of applications and looking at what I needed for each one. I soon found out that Snow Leopard support is somewhat spotty in many applications. In particular, the FineReader for ScanSnap software that I depend on so much for my scanning work flow is not fully supported. Fujitsu says that they will have an update soon and to keep checking their web site.

My password tool, 1Password, is another problem child. It works only on 32-bit Safari, and Snow Leopard now runs Safari in 64-bit mode. Of course, a new version is coming, and I will probably have to pay for it, but it is still in beta.

There was quite a bit of chatter on the Web about whether Adobe Photoshop Elements would work on Snow Leopard, and the responses seem split fifty-fifty for now.

Three very important tools were in danger of running in limited mode or not running at all, so I had to throw in the towel.

Time Machine saves the day!

As I sat, humbled, before my vanilla install of Snow Leopard, I admitted defeat. I slipped the Snow Leopard DVD back in the drive and rebooted from the DVD. This time, I selected the “Restore from Time Machine” option and turned on my Time Machine drive.

Guess what? It worked perfectly! Unlike many software products, Time Machine does exactly what it promises.

Within a few hours, my machine was fully restored to the way it looked seconds before I made my first attempt at Snow Leopard.

A Final Word

Learn from my mistakes, and my salvation by the full backup. As much as you can’t wait to upgrade, please do the following:

• Inventory all of your applications that you really need.
• Obtain the installation media (download or CD) for every single one.
• Obtain the keys for every single one.
• Investigate whether you need to export data from any of them, and make a checklist for these exports prior to upgrade.
• Check the “Unsupported Software” lists that are out there for any red flags.
• Check the web sites of your most important apps for their official word.
• And finally, do a complete backup!

It’s amazing how many applications and weird little utilities we forget we have. How could I have possibly remembered that I compiled a custom copy of the “rsync” executable for my backup workflow? I would have lost that and had to figure out how to rebuild it on Snow Leopard.

And I haven’t even talked about making sure your documents make it safely onto the new machine. That’s a whole ‘nother story.

In case I forgot to say it, please make a full backup.

[Update: I'm giving Snow Leopard a rest for a few months]

It has been said that Time Machine allows you to do a full restore from bare metal, and I’m living proof: I have done exactly that twice in the past week, with astounding success.

Encouraged by an episode of the Mac Geek Gab where they talked about their experiences upgrading their existing systems to Snow Leopard, I decided I would give the upgrade-in-place option a try. I expected some things to not work well and others to be quirky, but here’s what happened…

The actual install was painless, taking an hour or so to complete. I then began to kick the tires to see what was broken.

It was clear where those 64 bits went: apps like Safari were positively zippy, and I was pleasantly surprised with each new application I launched. All of my special settings seemed to make it through alive, including my password manager, though I did have to re-enter some of my registration keys. All of my mail and contacts made it through well. I was able to sync my iPhone without incident.

I found a few apps that weren’t working correctly and I looked for newer 10.6-compatible versions. I found newer versions of Yep and xGestures.

I did note that there is currently no ad blocker available for Safari that runs in 64-bit mode. This is disappointing because even though I understand that Apple wants us to see their ads, I can’t imagine that they really want us to suffer from the flickering jumping dreck that should have ended with the hated “punch the monkey” banners of years gone by. The fact of the matter is, if I want that 64-bit speed and snap, I guess I have to watch ads.

The Showstopper

I decided to scan a document to see just how difficult it would be to get my workflow going again. Michael F, below, wrote the truth about the situation: the scanner works fine in certain modes, but the OCR software doesn’t.

He pointed out that it was a problem of the FineReader software looking for a specific bit of metadata in the PDF identifying it as a ScanSnap PDF. Sadly, that metadata string changed.

The Finereader software is looking for “Mac OS X 10.5.8 Quartz PDFContext”, but under Snow Leopard, the string is set to “Mac OS X 10.6 Quartz PDFContext” instead.

There are ways to tweak PDF metadata, and one of them is by using pdftk.

I went to the pdftk site, all ready to download it and start OCRing my PDFs. I was greeted with less than optimal news: they have a version compiled for Panther, a version of OS X from several years ago.

I knew it wouldn’t work, but I gave it a try anyway: the app told me it needed Rosetta to run. I could have installed Rosetta at that point, but I figured I wanted a proper compiled version.

From there, I looked into compiling the app on OS X 10.6. I should have remembered my struggles with this several months ago on a Solaris Unix box when I found that pdftk depends on a monster called GCJ that required about forty other software packages to compile—it seemed a gargantuan task that I wasn’t ready to begin.

On a hunch, I inspected the content of a new pdf and an old pdf, the latter still acceptable to FineReader. Though much of the file was raw binary, the metadata was in text at the end. A short sed script was all it took to swap the nice text string for the offending 10.6 one.

In spite of my best efforts, FineReader still rejected my hand-tooled PDF file. It knew that it was a bogus file.

I have looked into Abbyy FineReader several times before, as well as Fujitsu’s ScanSnap support, and was unimpressed. For two vendors that produce products that are at the top of their class—FineReader is arguably the best OCR you can get for Mac, and ScanSnap is the best document scanner for the common man—they sure do have miserable customer support.

It is as if neither company cares a whit about the Macintosh platform or their customers. While most other vendors are busily patching their products and giving hourly updates on their Snow Leopard compatibility progress, Abbyy and Fujitsu just don’t seem to care that their best-of-breed combo suddenly doesn’t work on Mac.

Once they get this sorted out (hopefully in the next few months) I’ll give Snow Leopard another try. In the meantime, I’m sticking with good old Leopard.