mac diddy

I realize that this might be a massive understatement, but Mac users tend to be a little more enthusiastic about their platform of choice. So naturally as we are on the cusp of the release of Apple’s newest operating system, complete with great new features and promised performance enhancements, anticipation levels are high.

But it is times like these when some of us (myself included) need to be reminded that for all of the excitement around a new operating system release, upgrading your OS is not something to be taken lightly. There are plenty of potential pitfalls along the way and high hopes can turn into tears if you’re not careful. And so I present this non-exhaustive list of considerations before you go forward.

1. Wait!

Upon its public release, Snow Leopard will transition from beta to finished product, but is any current operating system ever really finished? Anyone familiar with Software Update on their Mac knows that realistically Apple will be working on this release for years, even after 10.7 hits the shelves. Although Apple does a very respectable job testing their software products in the beta phase, the real testing happens when it hits the market. Indeed, with the infinite complexities of real-world applications, the first release of any operating system is something of a glorified beta 2.0. Like the Grail Knights choosing to commence their journeys in the darkest, thickest parts of the forrest, early adopters face potential pitfalls and problems which are not always resolved with a quick Google search.

Of course if you’re like me, then waiting isn’t even a consideration – you want to stay ahead of the curve and even if there are problems, you want to know about them. But for a lot of users, the benefits of waiting for 10.6.1 or 10.6.2 should be considered. By then, Apple will have worked out some bugs in the OS and perhaps in the installer itself. Also, developers will have released some compatibility patches or perhaps new versions of their applications. Then there are the drivers for your peripherals… no guarantees that every device will be ready for 10.6 on day one.

As it stands, Adobe has not tested their Creative Suite 3 with 10.6 and have stated that they have no intention of support the CS3 with Snow Leopard. That doesn’t mean it won’t work… it probably will but it’s also quite possible that some functionality will be broken. Are you ready to shell out for their CS4 upgrades in order to remain productive? Maybe CS3 will just work and it won’t matter, but you can’t know until these things have been tested in the market at large.

2. Set aside some time.

OK, so like me you’re not going to wait. Well set aside some time to get things set up right and potentially troubleshoot some issues. If you keep in mind that this process might be a significant interruption to your productivity, then you’re less likely to greet potential challenges with frustration.

3. Backup, backup, backup!

I cannot stress enough the importance of backing up your data, regardless of whether or not you plan an OS upgrade. If left in service, every hard drive will fail eventually. But when you perform a system upgrade, there is always the potential for data loss which is not related to failing hardware. Pre-existing directory damage, installer bugs, bad installer media… not that these things are necessarily likely, but they do happen and when they do, you don’t want all of your data eggs in one data basket.

So before you get started, be sure that:

• All critical user data (pictures, music, documents, etc.) on the drive is backed up.
• All other critical data (applications, fonts, templates, preferences, network settings) is backed up or available for re-installation.

Ideally, you should clone your hard drive to be sure that 100% of the data and settings will be available to you later.

4. Be sure to have plenty of free space on the target drive.

Apple requires you have 5GB free. I strongly suggest more. If you have less than 10GB free, then chances are that free space is pretty well fragmented. Something I’ve noticed over the years working with Mac OS X is that when it gets low on space and fragmented, you start seeing significantly more directory errors and performance slow down.

I would go so far as to say that if you have less than 20GB free space, then you should consider upgrading your hard drive in the process. Storage is cheap and your need for more space is inevitable at this point, so you might as well take care of this before you upgrade. Otherwise you could be looking at doing it all again in a few months.

5. Clean up your target drive.

In the least, use Disk Utility to verify/repair the Disk Permissions and verify the volume as well. Ideally, you should also use a program like Disk Warrior to clean the disk directory. A squeaky-clean directory is going to up your odds significantly for a successful upgrade.

6. Type of install.* [Please see article update below]

The Mac OS installer gives you several options:

• Upgrade. This simply upgrades your current operating system, leaving your settings and user data in place. Easiest install type, but in my experience it also has the most potential to be buggy. With the considerable changes made to the working guts of 10.6, I’m a little more hesitant to recommend this option this time around, but we’ll see.
• Archive/Install.* [please see Update below] This option makes an archive of your current OS and installs a fresh copy of the new one. It also maintains all of your user data and settings with a pretty good degree of success. Overall I tend to use this option much more than a straight Upgrade because it is more thorough yet doesn’t usually require much more effort. That said, it is more likely that some applications might need to be reinstalled after using an Archive/Install. And because it doesn’t delete your old system, you will want to be especially certain that you have lots of free space when performing this type of install.
• Clean install. This is simply installing a fresh copy of the new OS on a disk which is blank or doesn’t contain an OS already. After doing this you will either move your personally data and install apps manually or use Apple’s Migration Assistant to pull your data from another drive.

Personally I’m a believer that when it comes to an OS upgrade, more is more. My systems tend to run squeaky clean and I believe it is because I tend to build my machines on clean installs and migrate the data back manually. It’s a bit tedious, but it seems to make for the most stable platform. Every other method is in my opinion something of a concession, trading potential stability for ease of install.

That said, if you’re well backed up, then there is no real harm in making that concession. Myself, I plan to perform an Archive/Install first and hope for the best. Then after a few updates to 10.6, I’ll do a clean install when time permits. Again, I remain skeptical about the straight Upgrade option. I saw enough issues with this option when going from 10.4 to 10.5 and so many of Snow Leopard’s changes are under the hood that I wonder if this time an Upgrade could possibly work better.

My final piece of advice is that you re-read section 3 – backup! Go crazy and make multiple backups. After all, if you make a single backup and then wipe your main drive, then you still have all of your eggs in one basket during the procedure. So have two drives for backups. This is truly a case where an ounce of prevention is worth copious pounds of cure. I’ve seen too much heartbreak when people learn this lesson the hard way.

Good luck and have fun with the upgrade!

*Update: Based on previous versions of OS X, I assumed 10.6 would offer all of the install options that its predecessors did. Turns out Apple has removed the option to Archive/Install. If you are installing to a blank disk (or a disk which otherwise lacks an OS), it will perform a clean install. Otherwise, the installer performs an Upgrade by default.