Migrating to Google Apps

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This is the story of my long road to Google Apps.

I got my first email account in 1994 at college. It lived on some ancient UNIX server so that had probably been around since shortly after the epoch. It was utterly reliable.

Later email addresses came courtesy of the various dial-up ISPs that I used in the 90s. These mostly worked pretty well too.

Fast forward to the late 90s. Hotmail become popular. It was flakey. It was filled with spam. It taught me a deep mistrust of web-based email providers.

I registered wincent.org and had my first, unedifying experiences with web-hosting. I shared a mail server with thousands of other customers, it fell over often, and when it did, there was nothing I could do about it. I learnt a deep mistrust of shared hosting.

By the early 2000s I had figured if you wanted something done properly, you had to do it yourself. I switched to a machine of my own in a co-lo facility. I learnt sendmail. It was a steep learning curve, but once everything was configured, it worked predictably and reliably, save for the odd hardware failure. This knowledge is now next to useless — I don’t think I’m likely to become an email ops engineer any time soon — but it was fun at the time.

Gmail came out in 2004 and I was uninspired. I still didn’t trust web-based email providers, and worse still, it was free; if even paid email hosting was crap, why would I even consider using free hosting? It was bound to be rubbish, and liable to get retired from the marketplace or switch to a pay-to-use model at any moment.

Time passed. I migrated to Rackspace, and then INetU, and finally to EC2. With each move, painful adjustments and migrations had to be performed. I moved from Courier to Cyrus when I updated my RHEL install, seeing as the latter was the default. The documentation sucked.

On EC2 I had to involve AuthSMTP because deliverability from EC2 IPs was said to be pretty poor. Another moving part, more custom configuration.

In 2011 I started working for Causes and experienced Google Apps in a business setting. Save for about 1 hour of down time, it has worked with total reliability for the better part of two years. In the same interval, EC2 has had multiple failures, including one big incident which had my instances out of action for several days. (Don’t get me wrong, I love EC2 and I think it’s awesome at the price; it’s ideal for small operations like mine.)

So, after all this, I finally admitted it was time to overcome my distrust of web-based email and accept that Google Apps is reliable, here to stay, and effectively free. The thing that pushed me over the edge was a desire to start using Google’s filtering instead of the built-in Mail.app filtering. I actually started to learn the Gmail keyboard shortcuts and try out the "Labs" features. It’s great.

I switched the other day and was able to get about 50,000 messages migrated over using the GAMME tool. It was not without its glitches and its gotchas, but it got the job done. Rather than stripping down my highly customized sendmail infrastructure back to the bare minimum, I just turned it off and replaced it with a vanilla postfix install on each of my EC2 instances (ie. for things like emailing cron job output). This allows me to tear down Cyrus, Sendmail, and Squirrelmail, making it considerably easier to upgrade my EC2 instances to newer operating systems.

I want to say that I should have done this before, but the truth is I am happy to be a "late adopter", coming in at a time when Google Apps has attained an awesome degree of solidity, polish, and nerd-friendliness.