April 18, 2014
Why is Email Hosting So Hard?

Rant incoming.

Ive hosted this website and several others like it for a long, long time. Along my journey, Ive lived as a lot of different types of sites, starting off as a virtual domain on someone elses host, moving to shared servers to being a reseller, and ultimately to dedicated VPSes (and briefly, a dedicated server). Ive run PHP, Python and Ruby against MySQL or Postgres on Ubuntu, CentOS, and Gentoo through Apache and nginx. I even ran a Half Life server for TF2 and L4D game nights.

But my white whale has been email. It is super hard.

Why? What makes email so much more complicated than its sibling services? I can run any of a thousand scripts to bootstrap a LAMP instance on my choice of hosting providers and be serving the net in minutes. But I cant do the same for email. And, heaven help me if I want virtual domains! Now were talking about complex things like a MySQL backend and some custom SQL for Postfix, if were lucky. Contacts and Calendar? Thats another story altogether. I can try my hand at Zimbra, but it requires extra connectors for iPhone sync. Maybe SOGo thats nice, because its written in ObjC, which I make a living writing. But, it doesnt integrate with mailsieve, which I used to set up rules.

I could always pay for Google Apps or Hosted Exchange, but thats expensive quick. My first use case is a family shared setup, so thats 8 users at $5 a month that they dont even really want, let alone to pay for. My legacy free GApps account doesnt support ActiveSync, and Outlook doesnt support CalDAV, so my parents machines are out.

Sigh.

I really dont know what to do. I can hack something together on Digital Ocean (I have before), but I need a fair bit of reliability. I could colo Exchange if the MSDN license supports it, but thats costly on a few fronts, so maybe Im better off paying for hosted Exchange. Oh, but I have a few domains that need email, so it has to be cheap.

Guide me, Internet. Suggest what to do here, because Im at a loss. Reliability is my number 1 requirement, followed by ubiquity on Windows, Mac OS and iPhones. Past that, Im your humble student.


March 25, 2014
Apple Speculation Time