Leaving Gmail Behind

For the last 8 years I have been using Gmail as my e-mail provider, during which 3 years I was a student. It was very convenient, inexpensive (cost-free!), and especially suitable for a student using various lab computers and stuck behind a fairly restrictive firewall (an anti-file-sharing measure). I didn’t have to worry about filtering spam or maintaining or paying for a server. Easy, easy, easy. This has finally come to an end.

That convenience kept me as a user after college up until now. As of two weeks ago I changed my e-mail address. You can find it listed below my portrait on this page (if you’re reading this on my website). Not only am I using my own domain name, but I’m running my own e-mail server. After attempting, and failing, at creating a decent setup with mu4e, I ended up following this guide:

It’s built around the superb notmuch mail indexer, which includes a powerful, fast Emacs e-mail client. Just from its technical superiority I’m wishing I switched to notmuch years ago. I’m now understanding for the first time why all those old fogey hackers like to use e-mail for everything: mailing lists, software patches, bug reporting, etc. E-mail a user interface agnostic system, giving everyone their own choice. The tricky part is setting up a decent interface to it.

Prompting the change

As you know, Google Reader shut down this past July. This left me using only two Google services: Talk and Mail. Not only is Talk easily replaceable — it has no significant data on Google’s servers — it will be shut down soon as well. I would need to move to a different XMPP server anyway. If I could move off of Gmail, I would finally be able to discontinue my Google account for good!

Why would I want to do this? It’s become increasingly apparent, especially this year, that there is very little privacy to be had when logged into a Google account. Various intelligence and law enforcement organizations have easy — likely automated — access to user data, especially e-mail. I’d really like to take that privacy back.

There are also the technical reasons. It’s a bit embarrassing to admit, but the final straw that pushed me to finally leaving Gmail was the new compose interface — a technical issue rather than a privacy issue — which was pushed out just a few days before I left. I found it to be very unpleasant and, worse, completely incompatible with Pentadactyl, as there is no longer a plain-text option (the one listed is a fake). A huge technical step backwards, towards the layman and away from the power user. I could do so much better than this.

Also embarrassing was being unable to have any meaningful use of PGP with e-mail all these years. That’s something I’ve always wanted to fix.

Brian was a guinea pig for me, because, between the two of us, he was actually the first one to move to his own e-mail platform. Seeing his success was a big encouragement for me. Not only could it be done fairly easily, but the results would be a huge improvement. This was all within my grasp!

A daunting task

Switching everything about my e-mail — provider, client, spam filter, server, domain — and running it myself would be a daunting task. There’s 8 years of archived e-mail to manage, though I kept it trimmed to a relatively light 1 GB of storage (which I cut down to 200 MB before exporting). I’ve made backups of all this e-mail on occasion, but I never had to worry about searching or actually using it. The backups were done “just in case.”

Gmail has excellent spam filtering, an advantage of having so many samples available, and I’m a complete newbie at dealing with it myself. Despite having my e-mail address published on this blog for the last 6 years, I surprisingly only receive about one spam message per day, so this wasn’t actually a huge risk for me.

Then there’s the issue of not looking like spam myself. My e-mail server needs to sit in a friendly IP neighborhood. I need to have a proper PTR record (reverse DNS). I need to generally look legitimate. No showing up to deliver mail to other mail servers in just a t-shirt. This is actually something I’m still struggling with right now. In fact, if I’ve sent you personal e-mail in the past and you’re using Gmail, you should check your spam folder right now, because something I’ve sent recently may likely have been caught in it. I don’t know why yet.

I would also need to learn the ropes of a new e-mail client. I used Eudora from 1995 to 2005, then Gmail up until now. Now, I’m the last person to be reluctant about learning how to operate a new piece of software. I’m constantly on the lookout for better software. The problem is that I use e-mail for a lot of very important things. I can’t afford mistakes. I need to hit the ground running on this one.

notmuch vs mu4e

Since I decided early on to go with an Emacs-based e-mail client, learning a new e-mail client got a lot easier. I know Emacs Lisp pretty darn well. In the worst case of getting stuck, I could very easily study the client’s source code and work out for myself whatever is going on. I could even monkey patch it in my configuration if it was causing problems for me (and I’ve already done exactly that).

I wanted to use the Maildir format, something I could hack on if needed. The two obvious choices for this were mu4e and notmuch, both started in 2009. I initially reached for mu4e. Compared to notmuch, it follows Emacs idioms more closely. For example, the e-mail listing is oriented around a mark and execute paradigm, like a dired buffer. After an initial glance, it felt more integrated.

Unfortunately, mu4e is still not mature enough for real productive use, making it far too risky for e-mail. I found out the hard way that the database format has varied regularly between versions. Worse, mu4e is not suitable for remote access. Not only does it assume the Maildir directory is on the local host, it uses absolute paths to access it, so it won’t work over sshfs as I had hoped. Bummer.

In contrast, the notmuch client is specifically designed to be operated remotely. Emacs doesn’t realize that it runs the notmuch client over SSH. Emacs doesn’t need to touch the Maildir directly. It’s a beautiful setup, one very friendly to versioning dotfiles. I’ve already done some pretty heavy configuration to get it exactly the way I want it. On top of this, notmuch is incredibly fast and stable. It’s been a very enjoyable client. So much so that it inspired me to build a web feed reader with a similar interface (to be described in my next post).

The mail server

My early plan was to run an e-mail server on a Raspberry Pi. It’s low-powered, making it very inexpensive and quiet to operate. It’s also very portable, so I wouldn’t need to lug a server around if I needed to move it — no more difficult than moving a cell phone charger. I could run it from my nightstand next to my bed if I wanted to. On the other hand, I would be a little nervous running my mail server on a residential connection. The downtime would be a product of my ISP, my power company, and my router. It’s not bad, but it’s risky when I’m worried about receiving important e-mail. If I was in the middle of job hunting I probably wouldn’t attempt it at all. Fortunately e-mail servers will retry over the course of several days, so I think this would generally be manageable.

This plan was struck down by Comcast’s network policies. The good news is that my IP address has not changed in years. The bad news is that they block port 25 both incoming and outgoing as an anti-spam measure. This makes it impossible to run an e-mail server, because e-mail must be received on port 25 (MX records were misdesigned feature). For outgoing, I would need to send e-mail through Comcast’s smarthost server, which brings up the privacy issue again. I assume the same organizations have this tapped as well. Even if port 25 wasn’t blocked, I wouldn’t be able to set a PTR record and my IP neighborhood would be suspicious.

I ended up going with Digital Ocean, as the linked guide suggested. The smallest, cheapest offering is more than suitable for my needs both as an e-mail server and an XMPP server. It will probably be handy for other short-lived, experimental servers too.

I used getmail to get all of my old mail onto the mail server in the Maildir format. It was completely straightforward and probably the easiest part of it all.


I can finally use GnuPG with my e-mail. An important factor in this setup is that encryption and decryption is done locally, not on my e-mail server. I don’t need to trust the server with my private keys. However, verification of signatures is done on the server, which is slightly less than ideal, but manageable.

I thought I might need to generate a fresh PGP key for this new e-mail address, but instead I learned something new about PGP. A key can have multiple identities attached to it, so all I needed to do was edit the key and add the new e-mail address. The PGP designers had already thought of this problem two decades ago! The updated key is linked next to my portrait, as well as distributed on the public keyservers.

I look forward to making more use of cryptography with my e-mail.

The old address

It will take me awhile, a year or more, to move everything off of my old e-mail address. I have a lot of accounts associated with it, many of which won’t allow me to change my e-mail address. So, in the meantime, anything sent there will continue to be forwarded to me. That’s now the only purpose of my Google account.

I’m a little worried about using my new e-mail address as my Digital Ocean account because it presents a circularity problem. I could easily get myself locked out of everything. I’ll have to figure out how I’m going to handle that situation. (Use my work e-mail address? So long as I don’t get locked out of my e-mail and get fired all at the same time.)

If you’re a hacker, I encourage you to run your own e-mail server if you’re not doing so already. It’s been extremely liberating for me.

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null program

Chris Wellons