Leaving Gmail

I’ve been meaning to do this as part of my Personal Security Audit project for quite a while now. It’s not that I don’t like Google at all but the power they gathered over the last couple of years with all their services made me feel quite uncomfortable. The same concerns apply to other services like Facebook as well, but that might be a completely different post.

So, first things first. The email server problem. I’d like to report on my experiences I had during that migration and what I ended up with.

Hosting my own server

When first thinking about this step I thought it was a good idea do cut loose from any third party email service and host my emails myself. This way, I’d have full control over every little detail of my server and I’d be independent from all the hosters out there. Ars Technica had an excellent four-part how-to on this topic covering everything from the basic system setup to two-factor authentication for your new service.

Naturally, when you take all the control for such an essential service, you also take over all responsibilities. This includes making sure that no one can access your server without permission, your server does not accidentally get blacklisted by other servers (and therefore your messages might get marked spam) and that you keep track of security issues, vulnerabilities and updates on your system.

I did not consider these burdens to be too bad of a trade-off. Until I actually tried it. I set up a server using the above mentioned tutorial and it seemed to be a lovely solution at first. Everything went smoothly and I was able to send and receive my emails with one of my domains. Ultimately, keeping track of all the Ubuntu and package security issues and fixing them on short notice turned out to be more effort than I was willing to commit to.

So this was not for me.

Hosting with yet another third party provider

A few of my twitter friends were looking for another email provider around the same time. Namely Winnie and Joggl suggested that FastMail¹ is “the place to go to.” So I thought I should give it a try as well.

First of all, I know that moving to another third party provider was not what I originally intended. Anyway, FastMail has a pretty liberal privacy policy written down in plain English. Also, they do not offer free accounts. This gives me kind of a safer feeling since I don’t feel comfortable being the product.² Besides, I already decided that going all-in on the self-hosting front was not for me. So I came to the conclusion that this might be a fair trade-off.

I signed up for their service and configured the MX records of one of my domains to point to their servers. The configuration went smoothly and I created a few accounts under that domain. The user interface is insanely fast and looks polished. In fact, I found myself using the web interface a few times this week when I could have easily fired up Mail.app.

Only caveat so far is the fact that the configuration on the client side is not as smooth as it is with Google or Yahoo mail accounts. These guys do have their configuration embedded into iOS and OS X while it does not know the least about FastMail’s servers. There does not seem to be any kind of auto discovery service, so the setup needs to be done manually.

Update 2015-02-07: I added a post about my configuration.

After my evaluation was done I decided that I should move my other domains and my main mail account over as well. FastMail offers an IMAP migration service which comes in handy when you want to move older mail accounts. For my main mailbox with ~6 GB it took something like 27 hours to migrate all the mails.

Some of my mails did not appear in my inbox after that migration so I worried that something went wrong. I contacted the support team about this issue and they quickly discovered that there was a problem with one of the timestamps that every message has. They ran a script to fix this and a few minutes later everything was back to normal. I contacted them on a few other occasions and they always replied within a few hours and answered all my questions. Some even in great technical depth.

I’ve been using this setup for about a week now and so far I’m pretty happy I finally made that move. I hope this will serve me this well at least as long as Gmail did.