Snow Leopard Installation Journey

Wow, long time between posts… well, no time like the present and I thought I’d share a my notes on the Snow Leopard upgrade in case it helps anyone else.

The rant

Firstly, the obligatory rant. I had a world of pain just getting to the install process. After my initial disc was promptly shipped out, it turned out to be from a bad batch. The first support rep recommended trying again and if it failed to call back and we’d try and archive and install. Luckily the rep that responded when I called back didn’t put me through that and just put me through to order management for a replacement disc. After an hour on hold, it’s quickly sorted out and I’m told it’ll be shipped out in 2-3 days. 3 days later I discover it hasn’t been shipped, and is instead queued for a refund. Another half hour on the phone trying to explain I wanted a replacement because it was faulty, and it actually does get prepared for shipment, arriving the Monday after the first one arrived.

The install

So, armed with working disc, I pressed forward. The install proceeded as advertised – it said it would take about an hour, and it did – up until it got to the “Less than a minute” remaining, which took about… 45 minutes before I gave up. It was apparent it had frozen. No choice but to hard power down. Rebooted and it booted into the Snow Leopard welcome – the install was successful, but I was stuck in the first time set up. Everything I tried left the registration step getting to the end with all the buttons disabled… so, onto the phone with tech support. Started by rebooting in safe mode which took a really long time but didn’t help much. So we stepped through the process anyway. As it turns out…

To skip the registration process, you can use Cmd-Q and select skip.

Not very intuitive, but I guess it discourages skipping it rather than having the button right there in the dialog. So, now I can create an account (must be a new one), and I’m logged in. Everything is still there (*phew*). Reboot into normal mode (takes an eternity to shut down), log in as myself and remove the newly created account. An hour into the call, now I’m all set.

Incidently, during frequent periods of waiting for the Mac to boot / shutdown I discussed the virtues of a clean install with the tech support, but am told that wouldn’t be possible with the Snow Leopard upgrade disc (apparently in contradiction to what I was told by the very first tech support and most of what is said on the internet – curious).

I found I’d freed about 12Gb during the process (measured using df -k to avoid being duped by the redefinition of a Gb) – a handy saving.

Checking it out, I found I had a new /Recovered Items directory which was unusual. I’m not sure if I just got this because of the missed completion of the installer. About 500Mb of data, including some things that didn’t make it (like the XCode tools). I’m holding onto it for now, but it looks like I shouldn’t need it.

Next, to see what survived the upgrade.

The Victims

I was well aware of what might and might not work after the upgrade. Here’s what I’ve found so far:

  • XCode command line tools
  • Dovecot
  • MailTags (upgraded to their 10.6 special version which seems fine)
  • Mail Act-On (was using 1.3, may need to pay to upgrade to 2.0 now)
  • The sync server in Omnifocus
  • The Omnifocus mail integration (re-installed from OmniFocus preferences)
  • iStat Menus (upgraded to 2.0, no problems)
  • Java 1.3 / 1.4 / 5
  • Visor plugin (relies on SIMBL, not re-installing)
  • Sort ordering in smart mailboxes in is not retained (no fix found yet)
  • X-Lite had no sound (upgraded to a beta version that seems to work)

I uninstalled a few other things that I wasn’t using any more to try and get rid of 32-bit system preference panels (though most seemed to be working).

XCode Command Line Tools

Oddly, gcc-4.2 and the other command line tools were moved to Recovered Items but most of the XCode installation survived. I planned to reinstall the new version anyway, which I tried. This failed about halfway through without much information other than to try again, which I did and succeeded. Go figure.


I had recently moved from MacPorts to Homebrew in anticipation of the upgrade, and all continued working afterwards except for Dovecot.

First up, it seems the dovecot user had disappeared during the upgrade process. Luckily, 10.6 seems to have included one by default, _dovecot in the mail group. So I adjusted the Dovecot configuration.

Next, failure to read /private/etc/ssl/certs/dovecot.pem – had just forgotten to use sudo when running launchctl. Try again.

After that, there was a period where it wouldn’t start and gave no error in the system log. To be honest, I don’t know what I did to fix that but when I came back to it later after some reboots it was working again. Reassuring.

Eventually got it started again but failed to auth from The system log showed:

7/09/09 6:37:36 PM	dovecot-auth[82]	in openpam_load_module(): no found
7/09/09 6:37:36 PM	dovecot[80]	auth-worker(default): pam(brett, pam_start() failed: system error

Seems that this has been removed in Snow Leopard. I’d been using the /etc/pam.d/dovecot file given here. I used the further recommendation on the page to remove that file and change the dovecot configuration to this:

passdb pam {
  args = login

After all that, my local mail server is back.

OmniFocus sync server

This one was a little unusual. The sync server runs a copy of Apache HTTP Server, which was failing to start up. The logs revealed:

[Mon Sep 07 18:36:30 2009] [warn] RSA server certificate is a CA certificate (BasicConstraints: CA == TRUE !?)
[Mon Sep 07 18:36:30 2009] [warn] RSA server certificate CommonName (CN) `mcbrett' does NOT match server name!?

While the short hostname of the machine was still mcbrett as before, it turned out that my installation pattern had changed the main host name to dummy's MacBook Pro 15" (dummy being the account name I created at first). I decided it was time for a change and changed my hostname to brettporter:

sudo hostname brettporter
sudo scutil --set HostName brettporter

Along with the same change in the Sharing system preferences, this was enough to get the sync server started again.

The Verdict

Other than these, my apps (including some that had received bad reports from others) seem to be working fine.

This was a much more painful upgrade than Leopard (salt in the wounds from the painful ordering process). The disk space saving is nice, but it never lasts 🙂 So far I haven’t noticed much in the way of performance improvements and have still obtained the marble of doom – time will tell if it seems to have improved or not. I’m particularly interested in Time Machine performance.

The big wins probably won’t come until applications start to take advantage of grand central and so on. All in all that is what appeals to me most about the release – most developers would love the opportunity to take some time and just clean things up in their projects and build out the core support.

4 responses to “Snow Leopard Installation Journey

  1. Hi,

    thank’s for the dovecot info.
    I’m using MacPorts and the info solved my problems.

    Thanks again

  2. Hello,
    I have been relentless trying to install Dovecot on leopard and failed repeatedly. I might upgrade to Snow leopard.

    By any chance, could you post(or email) your dovecot conf files?
    Thank you

  3. Pingback: Obligatory OS X Lion Installation Post | Brett Porter

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s