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The Disaster-Free Upgrade to Mac OS X -- Part 2

by Derrick Story

If you approach operating system upgrades like I do, then you've thought long and hard about the move to Mac OS X. That's good, because I think we need to be discriminating about what we load onto our computers and why we're doing it.

When people ask my advice about switching to new software, my first answer is usually: it depends. It depends on your computing needs, hardware, budget, and the amount of time you have for testing.

If you're still not sure that the time is right to upgrade your PowerBook or your iBook, then I think you should consider reading, or re-reading Disaster-Free, Part One. The article is designed to help you come to the right decision for your particular situation.

That being said, if you are ready to upgrade, and you follow the steps in this article, I feel confident that you will have a smooth transition to Mac OS X. In part, this is made possible by Classic's ability to competently handle your existing applications.

Quite honestly, without Classic's backward compatibility, I would have a hard time recommending the Mac OS X upgrade for most people. Fortunately, Classic is a well thought-out transitional environment that eliminates most of the risk of switching to an entirely new operating system. In fact, some of my existing OS 9 apps actually run better in Classic.

Before we get started, however, I have a little housekeeping. Since I published Disaster-Free, Part One last week, a couple of positive things have happened:

Comment on this article Mac OS X seems particularly appealing to laptop users because of its networking flexibility and fast start from sleep. If you've taken the leap to Mac OS X on a laptop, what tips do you have for others considering this migration?.

So, now that the house is cleaned up, let's get to the upgrade!

What you'll need on hand

Related Reading

Mac OS X: The Missing ManualMac OS X: The Missing Manual
By David Pogue
Table of Contents
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This is an article about laptop upgrades. As such, I'm sticking to the criterion of having an Airport-compatible PowerBook or iBook. This stipulation will change as soon as there are good third-party drivers for 802.11b networking cards. But for the moment, AirPort is the way to go.

Make sure you have enough RAM, at least 192 MB -- get more if you can. If you skimp on RAM, you'll force your Mac to frequently access the hard drive as it attempts to muster the virtual memory it needs to complete the requested task. The end result of that scenario will be that you'll think that Mac OS X is a dog. Get the RAM you need and avoid the fleas.

I recommend that you back up your entire laptop hard drive -- everything. In my case that was 5 GB of data (ouch!). Fortunately, I have a 6-GB FireWire drive that I can use for this project. But what if you don't have one available?

If you have access to another FireWire-enabled Mac, there's a nifty trick that allows you to directly access its drive from your laptop. It's called target disk mode. I learned about this thanks to a note from Brian T. Nakamoto.

Brian sent me this Tech Info Library link, How to Use FireWire Target Disk Mode that describes the steps involved to directly access the hard drive on another Mac. Very handy.

If you don't have access to another FireWire Mac, or an external drive, then you have to get creative in order to back up your old OS and its related files. Of course you can skip this step, but doing so eliminates part of your safety net.

Have enough hard drive

Speaking of drives, I really like having a little "head room" on the internal drive of my PowerBook. I had a 6-GB IBM drive, and it just wasn't enough storage for my regular work, let alone for this upgrade. (If you already have a nice 10 or 20 GB drive, you can skip this section.)

So I ponied up the couple hundred bucks to buy an IBM 20-GB internal drive and installed it myself. The install went smoothly even though I hadn't changed drives in this particular laptop before. My only pearls of wisdom are:

Once the new drive is installed, you're ready to pull out your Mac OS X CDs and upgrade.

Preparing the drive for Mac OS X

I'm sure you thought we'd never get to this point. By now, you should have all of your data, applications, and system files backed up on another drive, and you're ready to either wipe your existing laptop internal drive or format your new one.

Boot your computer from the Mac OS X CD and run the installer. Once the installer has booted, you have the option of running the Disk Utility (Installer Menu --> Open --> Disk Utility). Launch the utility and create two HFS+ partitions. I called one "Mac OS X" and the other "Mac OS 9." The first partition is where we're going to load both Mac OS X and the Classic OS 9.1 environment. The second partition is where we'll load our old environment, including our existing 0S 9 operating system.

If I were to do this step over again, I would make the Mac OS X partition larger than the other, since that's where I'll be adding new apps and files in the future. As it turned out, I made both partitions 10 GB. I have a feeling I'll have lots of extra space on my Mac OS 9 partition. It's not that big of a deal however, since I can copy files from one partition to the other.

Now that you've created the partitions and installed the Mac OS X drivers, quit the installer, shut down the computer, and replace the Mac OS X CD with the Mac OS 9 CD, then reboot with the OS 9 CD.

Now you're ready to install Mac OS 9.

Installing the operating systems

By the time you're finished, you'll have installed three operating systems on your internal drive: OS X and OS 9.1 on one partition, and your old OS 9 environment on the other. If that sounds excessive, understand that this is where the "disaster-free" guarantee comes into play. The redundancy allows you to play with the new OS as time allows while still being able to perform your daily tasks as before.

First you're going to install the version of Mac OS 9.1 that came with your Mac OS X upgrade. This will be your Classic environment that resides on your Mac OS X partition.

After Classic is installed, switch to the Mac OS X CD (reboot with it) and install that operating system on your OS X partition. I like to use the Custom Install option so I can see everything that's included. Be sure to choose the BSD goodies (BSD subsystem and additional print drivers).

Also, I highly recommend installing the Developer Tools as part of your package. If for no other reason, do it to get WorldText and Sketch. They are both terrific applications that anyone would want. You can find them in:

Developer --> Applications --> Extras

You're two thirds of the way home now. Reboot your Mac off the internal hard drive. The easiest way to do this is to hold down the Option key during restart. You'll get to choose which OS you want to boot with.

Now you're ready to add your old operating system and applications to your laptop. In my case, I plugged in the FireWire drive and my PowerBook recognized it immediately in Mac OS X. I copied the entire contents of the old drive to my Mac OS 9 partition on the laptop

Talk about made in the shade. Your Mac now has OS X, Classic, and your old environment all loaded and ready to go. So how do you choose between them?

Simply go to System Preferences (it's on the dock) and choose Startup Disk. Your Mac will scan your hard drive for viable startup folders and present them to you in a dialogue box. You simply click on the one you want, then restart.

Screen shot of Startup Disk system preferences.
You can simply choose your startup environment in the Startup Disk system preference.

Just so you'll have complete confidence that you haven't lost anything, go ahead and choose your old system on the Mac OS 9 partition and restart. Viola! It's just like your old baby. The only downside for me was that I had to reestablish all of my alias connections and tidy up the desktop a bit.

To return to Mac OS X, go to the Startup Disk control panel, select Mac OS X, and restart. Boom! You're back in Mac OS X.

What I've learned since upgrading

I have just a few personal comments resulting from my life after the upgrade.

First, I'm really glad I have my entire "old computer" on the other partition. I've gone back to it many times to search for an old e-mail or find a stray graphic. I highly recommend that you give up the disk space and save your old environment -- especially if this is your main computer.

Second, the Carbon version of IE 5.1 that comes with the upgrade isn't very good. I recommend that you download OmniWeb 4.0 which is a beautiful, full-featured browser written in native Mac OS X. You can try it out, and if you like it, the license is $29.

Also, if you're in an 802.11b networking environment that isn't from an Airport Base Station, you may not be able to connect using your regular password. If you enter the Hex version, however, it works. I don't know why. To get the Hex conversion, you can download BBEdit which handles those conversions for you.

If you use QuickTime, Mac OS X provides you with version 5. Pro users will be disappointed to learn that their registration number for Pro version 3 and 4 doesn't work with version 5. You have to pony-up the $29 for a new registration number for version 5, or use your old version of QuickTime in the Classic environment.

A final word of caution: the Aqua interface is addicting. I've found that if I can accomplish a task in Mac OS X, that's what I use because I love the dock, graphics, and the overall feel of the environment.

Beware of false economy

This approach to upgrading to Mac OS X is a conservative one. There are lots of corners you could cut, but is the money you save worth more than your data or the time that you waste trying to figure out work-arounds?.

What I've tried to create is a very safe environment for migration so you can begin learning about Apple's new operating system without worrying about losing valuable data or functionality. I hope you have the opportunity to give it a try.

Derrick Story is the author of The Photoshop CS4 Companion for Photographers, The Digital Photography Companion, and Digital Photography Hacks, and coauthor of iPhoto: The Missing Manual, with David Pogue. You can follow him on Twitter or visit

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