Adapting to Mac OS X Lion 3: Being extra careful when upgrading

I wonder how many people have upgraded an operating system only to either have a major failure trash their disk, or else to find that critical applications do not work. One can find people with such war stories no matter what the operating system. Upgrading Mac OS tends to be relatively painless for most people, but one can search the web and find plenty of people who had bad experiences. Sometimes, they even have reported going back to Snow Leopard. I think some people do this unnecessarily: Lion speeds up after a few hours, and most application issues can be resolved.

I set out to be very careful when converting to Lion. In this post I explain the precautions I took, and how the upgrade worked out. This is my third post on my conversion to Lion, my first two posts are here (on my dislike for 'natural' scrolling) and here (on issues with apps).

As I explained in an earlier post, I am meticulous about backing up my Mac on a daily basis. I use Time Machine when at home, and also maintain a bootable copy of my main disk with SuperDuper, both at home and at work. I update these using 'Smart Copy' after every OS update or major application update.

Before upgrading to Lion, I took several extra steps:

1. Testing the backups: I actually booted off my SuperDuper partitions and tested the system for a few minutes. There is no point having a backup that turns out not to work.

2. Separate backups of cloud-synced data: I made separate backups of certain key data. In particular, I backed up all my calendars in iCal by exporting them to .ics files; I also exported all the contacts from Address Book. Why? I have had bad experiences with cloud-based storage. I will post on this in more detail at a later date, but the short answer is this: If anything goes wrong with the cloud-based syncing of your data, the cloud could lose its data and sync empty data back to your computer, wiping it out. This actually happened to me during an update to MobileMe last fall. Luckily I had backed up my calendars and could quickly reinstall them. Time machine and SuperDuper backups are not so simple to use for this type of restore process.

3. Keeping a permanent Snow Leopard partition: I made an extra partition on my external disk at work and created yet another bootable copy of my entire disk. However I called this 'Snow Leopard'. My intent is that I will never update it to Lion. I will keep it around for a year or two in case I ever need to run an app that turns out not to run in Lion. I will, however boot into it whenever Snow Leopard security updates are issues, and also to periodically update  Norton Anti Virus definitions on it. To make the partition I used iPartition. Once again, I tested this backup by booting into it.

An important point about making my Snow Leopard partition: Before creating it, I went to the MobileMe systems preference panel and set it to sync manually. Why? Because whenever in the future I might temporarily boot from this partition, I don't want the computer to spend an age syncing my calendar, address book and so on. This can actually be a major problem when accessing an old backup.

4. Saving the installer: After downloading Lion from the Mac OS App Store I did not press 'Continue'. Before doing this I went into the Applications folder and copied the 'Install Mac OS X Lion' to my backup disk. That way, if I ever have to reinstall from my backup, I don't have to download the 3.6GB installer again.

I actually had a small scare while downloading Lion. I lost network connection briefly when the installer was almost completely downloaded (unplugged the cable - my mistake). A message was displayed saying that the App Store app could not connect to the store. I clicked on the download button again, expecting the download process to have to start again from scratch, but it just picked up where it left off. Very nice.

The installation went without incident; it took a little longer than it 'advertised', Expect 10 minutes more than the installer promises.

After the installation I tested all my apps and dealt with a few issues discussed in my previous post. Lion ran extremely slowly for the first few hours while Spotlight indexed the disk. After that was complete, I  backed up the latest installation to my SuperDuper partitions (except the Snow Leopard one).

In my next post I will discuss my opinion about the usability of new Lion features.