The Continuing Quest for Reliable Email

I have, for some time now, run my own Internet domains for purposes of having what are essentially vanity email addresses and web sites. The longer I’ve done this, however, the more picky I’ve become about what kind of service I have my email stored on. I use, primarily, IMAP to access my mail, but I do on occasion require a good web mail client for those times when I don’t have my own computer(s) available to me.

In the past, I have made due with borrowed capacity on other people’s servers, running my mail through UW IMAP or Dovecot IMAP or even Courier-IMAP. All three are very capable, stable IMAP servers, though I’ve had the most reliable mail with Courier over the years. For a web front-end, if there’s been one, it’s usually been either SquirrelMail or IMP. Both are serviceable, though SquirrelMail tends more towards the no-frills just-get-me-my-mail-please approach, whereas IMP has tried for a long time to be a flashy, high-class webmail package. Neither one was really good enough, in my eyes, but then again, I’m tough to please for web apps.

The most important thing of all for me for email is reliability and stability. After that, I look at things like “how hard is it for me to manage” and “does it also make my wife happy?”. It’s on this third point that I started becoming restless with the options I had available to me, and started looking with some envy at Gmail. Zimbra, too, was under serious consideration, but it’s a heavy enough application for a server that I could not simply toss it on someone else’s server when I was already getting access for free.

So a while back, along came Google with Gmail, and everyone jumped on it. Starting off with 2GB of storage per account, and now steadily climbing (I think my account has a 6.7GB cap, and it seems to go up all the time), email pack rats now had a place where they could send all their mail and not care. It’s fully searchable, you can put multiple labels on a message (kind of like filing a message in a folder, but not really) and Google has some very good spam filtering. When Google introduced IMAP access, I did some testing and then moved all my mail over, taking advantage of Google Apps for Domains.

Right away, there was a big glaring pain-in-the-ass: Google Mail’s “All Mail” folder. From the web interface, it makes perfect sense, but when Google created their IMAP implementation, it was apparently decided that all labels would be presented as if they were IMAP folders. This includes both the fixed, standard labels (Inbox, Sent Mail, Spam, Trash, All Mail) and the user-defined labels would all be listed as folders. Additionally, the fixed labels (excluding “Inbox”) would all exist under a “[Gmail]” folder. Most people ended up renaming all their labels to be prepended with “[Gmail]/”, and then setting their IMAP Path Prefix (or IMAP server directory, or some other name depending on IMAP client) to account for everything being under that “folder”.

But there was that “All Mail” folder on the IMAP server. And it was exactly what it claimed to be: a folder containing all your mail, sans spam (which was in the Spam folder only.) This meant that any IMAP client that wanted to download full message data not only needed to download the copy that was in Inbox, or in a label/folder, but the second (or third) copy would get downloaded from All Mail, as well. The potential for enormous bloat for clients that downloaded offline copies of email is quite impressive, when you can have over 6.8GB of mail in your Gmail account. It bogged Mail.app down so badly on my wife’s iBook that she simply refused to use it anymore, and has just been using Gmail directly. Her poor little iBook was trying to download some 650MB of email, twice. That’s the side-effect of Google’s “All Mail” folder.

She’s told me she doesn’t really mind, but I get the sense that she’d be much happier with Mail.app, and it’s integration with iCal and Address Book. It just works better, especially when she doesn’t have any contacts in her Gmail address book. As an IT professional for the last 10 years, especially as one who’s maintained large mail systems, I could do better for her (and myself).

Now Apple is announcing a re-launch and re-branding of .Mac, Mobile Me. This is primarily interesting to me because we’re planning on going for iPhones when our Sprint contract is up this summer, and the capability for over-the-air data synchronization is almost worth the $12/mo it would cost us for a Mobile Me Family Pack. The obvious side benefit would then be that we’d be able to sync our data between our respective laptops, iPhones and desktops nearly thoughtlessly. Basically, if they’re on an Internet-connected network, they’re synced to the latest data. That’s cool.

But there’s a mail service as part of .Mac and MobileMe. An IMAP mail service, with a web front-end that looks an awful lot like the Mail.app that I know and love and hammer on daily. Interesting. Sure, there’s 20GB for me to upload web pages and iPhoto galleries and movies and whatnot, but if the service includes a mail service, IMAP at that, and “Push” IMAP if you’re using an iPhone, this could be worth looking into! Sure, I’d need to set up something to handle mail addresses for our vanity domain(s), and forward them on, but it might be worth the hassle.

But .Mac/MobileMe doesn’t support mail filters or rules on the server. You have to run them in the mail client. This, to me, kind of defeats the purpose of an IMAP server. I want to be able to have all the rules run on the server, so that it doesn’t matter at all what client I use. If I have to use the web to check my mail, I don’t want to have to wade through everything my rules would have sorted.

Part of the reason for this, I suppose, is that Apple expects you to always be using one of your Macs to read your mail (or, I suppose, your iPhone, though I’m not sure Mobile Mail actually processes mail rules.) It still seems to me like the .Mac/MobileMe mail service is a bit lacking for a power user like myself. What concerns me the most, however, are things I’ve heard regarding .Mac’s issues with reliability for mail delivery, even for messages you send through .Mac.

Zimbra, the mail system we’re migrating our department to at work, is a supremely solid IMAP (and POP3) server, that also just so happens to be a reasonably good web-based collaboration server with integration for all the major desktop platforms. We’ve been using Zimbra at work for nearly a year now, and I really have nothing but good things to say about it. It does what they say it’ll do, and it’s an extremely stable mail platform.

You need to pretty much dedicate a server to it, though, so it’s not something you can load on to a shared system. If you don’t have a server to through at it, though, there are a number of vendors who resell Zimbra accounts either individually or for hosting your whole domain. Luckily, I happen to know someone who’s doing reselling, and since I maintain our Zimbra installation where I work, he’s letting me have it at cost for the licenses I use while helping him with whatever questions he has. Seems like a good arrangement.

As happy as I’ve been with Zimbra at work, I’m almost positive that I’m simply going to move our email to Zimbra and off of Google. Need to set up a reliable test first, though, so that I can demonstrate the system to my lovely wife and get her reaction to it. That part, however, is proving to be a trial, and I’m not entirely sure why yet. More to come in a future post.

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The Continuing Quest for Reliable Email

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