It only took me about 3 weeks but I'm finally running Mavericks, the latest version of Mac OS X, on all my computers! You might think being a big Apple fan I'd be first in line to install it. But sometimes there are good reasons not to be so eager to upgrade.
First, I use MacBook Pros both at home and work, and am running a number of non-Apple applications. At home I run VirtualBox and Parallels, virtualization applications that allow me to run different operating systems on my Mac, such as Windows and Linux. I occasionally use these applications when friends need help with their Windows machines (it came in handy recently when I helped a friend install Boot Camp). I also use Quicken to track our finances. I started this back in the early 1990s on Windows. When I started using Macs over a decade ago, I looked into switching to the Apple version of Quicken. Unfortunately Intuit has never done a good job of supporting Quicken on the Mac and I realized I would lose large amounts of historical data if I made the switch. So I use Parallels to run Windows XP, so I can keep using Quicken. I also do taxes for family members and friends, and some of them have complex tax structures like trusts that aren't supported in the Mac version of Turbo Tax, so I use Windows XP to run that. Given this, I want to make sure there aren't an incompatibilities with the new OS and my 3rd party applications.
Second, no matter how much beta testing Apple does, there are always issues. There are some problems that don't crop up until you have hundreds of thousands of users running the system. This year, one of the biggest issues was between Mac Mail and Google Mail (this issue was discovered during beta testing but I didn't hear about it until after the general release). This was an issue for us, as both my wife and I use Mac Mail to manage our Google Mail accounts, so I didn't upgrade until after Apple released a patch to fix it on November 7.
Third, I'm not just upgrading one computer, I have 3 computers (plus a 4th if you include a test laptop I have). And it's not just installing the new OS, there are backups that need to be done and updates afterwards. So it ends up taking me quite a bit of time to get everything to the latest release.
What this all means is I am cautious when upgrading my computers. Below is a summary of the steps I took to upgrade my computers.
I waited about a week before starting to upgrade. I watched the tech press to see what issues were being found and if there were any major incompatibilities. I found a good Ars Technica forum post with a list of known Mavericks incompatibilities, and I didn't see anything major. I was aware of the Google Mail issue, which slowed me down, as I wanted a fix for it before I upgraded my wife's and my main computer.
The first machine I upgraded is what I call my "test" machine. If you read my previous post on restoring from Time Machine, my test machine is the one I spilled coffee on and had taken it for dead. It turns out it survived, and since my company gave me a new laptop, I have this extra one. I've had a couple minor issues with the computer and don't know how long it will last, but for now I love having an extra machine I can try things out on! Being a test machine, I didn't do any of the usual backups I'd normally do. Before the upgrade I had taken the latest Time Machine backup from my main computer and restored it on this computer. I downloaded the Mavericks installation app (and saved the install app to a flash drive so I wouldn't have to download it again) and installed it.
The installation went well. After upgrading and logging in, I had to enter my Apple ID password to reconfigure iCloud. A new feature in Mavericks (and iOS 7.0.3) is iCloud Keychain. I had to enter my 4 digit security code that I used when I configured Keychain on my iPhone, then enter the verification code that was sent to my phone. I also had to install Java (since I primarily develop in Java, it would have been tough to do my job without it), and reconnect my Dropbox and Google Drive. For Google Drive, I had to first disconnect my account as I didn't have a local Google Drive directory (I don't back it up to Time Machine, so when I did the restore it didn't create it). When I signed back in, it recreated the local directory and began resyncing.
Shortly after, I checked for software updates, and installed updates for Pages and iPhoto. A new feature of Mavericks is to automatically download and install updates. The first time you receive an update you will be prompted to turn this feature on.
The second machine I upgraded was my work computer. I did this after a few days of using Mavericks on my test computer. I don't use Mac Mail at work, just the Google mail website, so I didn't have to worry about the Mail bug. Prior to upgrading, I made 2 backups. I discuss this in my backup strategy blog post, but to summarize, I make sure my Time Machine backup is up-to-date, and also do a full backup with SuperDuper!. I then booted from the flash drive image I had made on my test computer and installed the new OS. Again, I didn't run into any major issues. I had to reinstall Java, plus some other tools like Maven, Homebrew and the Xcode developer tools.
Once Apple released the fix to Mac Mail, I then upgraded my main computer. I spent a couple of days using the system and making sure Mail was behaving properly, then I finally upgraded my wife's computer. One of my measures of a successful upgrade is how much my wife complains. I usually upgrade her computer without telling her, then wait a day or two before asking how her computer is running. In the case of Mavericks, as was the case with Mountain Lion last year, she didn't even notice the change. I think this has to partially do with not upgrading immediately, but instead waiting for a few days. This alerted me to the Mail bug, which, if I had upgraded before getting fixed, would have caused us a lot of issues.
I'll hopefully post an update later with some of my initial thoughts and experiences with Mavericks.
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