12 February 2010

Switching Email

I just took a couple of steps in the email world: I switched both my server and client.

I blame Apple. They announced iPad, and I’m making sure I’ll be able to fully use it.

For various reasons, I have multiple email accounts. Until now, I’ve been reading some with Apple Mail on my Mac, and also on my iPhone. The accounts are set up to use IMAP, which means mail is on the server (or if you will, the cloud). I can get it anywhere.

But for my oldest accounts, I’d used Eudora as my client, and Eudora Internet Mail Server for the actual server I ran. And I’d set things up with the POP protocol (which is essentially client-centric). This meant that I needed a master device that sucked the messages off the server. I couldn’t retrieve mail from my iPhone, because my laptop was the master owner. And EIMS didn’t support SSL anyway. EIMS also supports IMAP to the standard, and Apple Mail is apparently buggy, and doesn’t play well with EIMS.

I thought about buying a mini with Snow Leopard Server and running mail off it. That would give me the cloud and the security. But it costs $1000. I might have been able to add SSL on top of EIMS, but I’d still be dealing with the mismatch between it and my IMAP client.

What I ended up doing was using Google Apps Standard Edition. I don’t care about the actual apps (Calendar, Chat, Docs), but they do provide what is essentially Gmail for your domain. In my case, domains (since my wife and I get mail at three different domains). Although they push for the Premier Edition ($50/year/user), the free Standard Edition provides domain aliases (so we can handle our three domains via the same site) and nicknames (so I can have app-specific addresses).

Basic setup was easy. I had to prove I owned my domain, which I could do by putting a file on my server. The domain aliases were a bit trickier — Google checks for “domain.com/file” but I’d set up Apache so it was actually at “www.domain.com/file”. There was no error message — and since it’s free, support is only via a forum (which I still haven’t gotten an answer from). But I eventually figured out what was going on. But then, one of the domains took, but the other did not. (After several hours, it finally did.)

Google provides a way to test things, so I created an account on my iPhone and made sure I could send and receive via IMAP.

I don’t do my own DNS so I had to contact my ISP. They threw the switch, and things pretty quickly were working!

While I get no spam on my Gmail account, I get a fair amount to my older addresses (the fact that it’s multiple addresses probably works against me). Google has so far filtered all of this about as well as SpamSieve did on the client side — I get a bunch that’s not blocked by the server, and (being paranoid) go through it for false positives on occasion. (I have gotten two false positives in almost a week.)

On the client side, I had to learn Gmail’s idiosyncratic approach to IMAP. You will need to enable the advanced IMAP controls via Gmail Labs, and expose the labels. Then the important thing, if you want things to look more or less like IMAP, is to ensure that any message has only one label. I had originally used the tagging model, and assigned labels liberally. After all, Google wasn’t duplicating a message in the In folder and the Developer folder. But IMAP (at least as implemented in the Apple client), does.

Luckily, it’s easy to set up your filters so that an incoming message that’s filtered skips the inbox. At this point, the IMAP client can move things between folders, and the right thing happens. Well, you’ll probably want to read Google’s documentation on how to set up for IMAP, since some of the system folders should be set up in a less intuitive way.

So far I’m pretty happy with this. As far as I can tell, it’s been totally transparent — I still get and send email with the same addresses. I can get mail via IMAP or the Web-based Gmail interface. And I’ll no longer need to administer my own server (as easy as that was with EIMS).

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