Email problems are server problems

I used to be a Mail hater. I hated the amount of spam I was getting, the difficulty I had accessing my mail when on the go; the sweet time Mail.app took to perform even the simplest of tasks. I was pretty desperate about finding a new mail client; I planned to produce one for a long time, and I even switched to using Outlook 2007 in Parallels for a while.

Then I switched mail servers, and all my problems went away.

Some background: for the past 12 years or so, I’ve ran my own email server. At first, it was the usual open source fare of sendmail + a random pop/imap server; then I graduated to cyrus, and finally, to Mac OS X Server, which was supposed to wrap cyrus and other components up in a nice user interface.

But those servers didn’t really work all that well. They were a chore to manage — even the mail service in Mac OS X Server had a bunch of obscure configuration files and dependencies deep in the system itself — and stuff like spam detection, mailing lists and web mail were half-assed at best.

Then, a few months ago, I decided to migrate our company over to Kerio MailServer. There are three aspects to it that have totally transformed my email experience.

First, Kerio’s spam filtering works, out of the box, exactly like you dream it should. The server, on its own volition, moves email to your Junk folder if it thinks it’s spam. Also, if you manually move a message to Junk, the server’s spam filter learns to consider that message spam. Conversely, if you move a message out of the Junk folder, Kerio understands that it’s not spam, and adjusts its filtering accordingly.

The freakishly cool thing about that is that it allows Kerio and Mail’s own junk filtering to learn from each other. If Kerio moves a message to Junk, Mail learns from that; if Mail moves a message to Junk, the server learns. And by manually moving emails in and out of the Junk folder, the user can teach both Kerio and Mail simultaneously.

The second Kerio killer feature is that it’s trivial to specify all of your mail rules on the server, rather than in Mail. You just log in to Kerio’s web mail interface and specify the rules with an easy-to-use rule builder. This, together with the great spam filtering, means that you are able to access your Inbox on a variety of devices, and only receive the messages you are interested in: not spam, not the mailing list messages that you have set up to end up in folders.

Finally, Kerio implements Microsoft Exchange’s ActiveSync protocol for syncing. It includes an iSync plug-in that syncs my Mac’s Address Book and calendar events to the server. My Nokia mobile phone has a client for ActiveSync called Nokia Mail for Exchange. With it, my phone gets pushed new emails, calendar events and address book entries automatically over the air, without me having to ever sync my Mac and the phone explicitly. It all just happens.

Because of these three features, almost nothing about my email use is now the same. These days, only a dozen or two emails a day end up in my Inbox. That’s few enough that I read and triage all of them on my phone as they arrive (since the server is pushing them to the device, I get them instantly, rather than after a specified interval). Then, when I’m on my Mac, I reply to the messages that survived the triage (ie. weren’t deleted on the device), and file them away. Bliss.

Actually, there was one bit of hackery that I had to do myself. Both Mail and the Nokia mail application are lousy at actually deleting email from the IMAP Inbox; they mark the messages as deleted, but never purge them. This is not a problem when you use Mail exclusively, but a lot of other email apps, the Nokia one included, display non-purged deleted emails struck out in the inbox.

Again, bliss.