the foobar zone

Off and on over the years, I've used a variety of email systems. Elm and Mutt were early favourites, and it took me until 2001 to go beyond text based systems. it wasn't that I had a great liking for text based systems, just that the GUI MUA's at the time were pretty trashy.

Evolution gave me a good run for money, until late 2006 when I finally got fed up onto the back teeth of Gnome's masochistically awful library management and bought myself a shiney new mac. Thunderbird I have been using since the early days, but mostly at home on Windows, and until recently, it's been my MUA of choice on OS X. I started up Entourage once or twice, but it narked me off when it automatically started doing funky stuff with certain messages in my inbox. Also, it doesn't support threaded mail reading in any sensible fashion, which is a complete show-stopper in my books. It's also a PPC application, which means that it runs under Rosetta, and that means it's slow. This will be fixed in Office for Mac 2007, but that's not due for several months.

Finally, I gave Mail.app a shot. I had shied away from it until recently, mainly because of problems between the chair and the keyboard, but there were a couple of problems on Thunderbird that were really beginning to annoy. The first was that there was no real attempt to integrate with various OS X features like Spotlight, Keychains and the system Address Book. Worse still was the fact that there is no writable LDAP address book support on the system, which means the keeping any sort of consistency between address books on multiple systems is just pain. Call me lazy, but I've really lost interest in doing quirky systems stuff which really ought to work properly out of the box.

So, Mail.app, here we come. The first thing of note is that it pointed out that my self-generated mail server SSL certificate was broken, and had been for several years. Oops! All other mail clients had the lazy option for "Accept this certificate permanently", which was duly ticked on day one. But not Mail.app.

Ok, so CA Cert to the rescue. One pretty X.509 cert installed on the mail server and a copy of the CA Cert root certificate jammed into Keychain, and that problem bit the dust.

Mail.app supports TLS fairly well, which is important because I explicitly prohibit unencrypted authentication tokens on pretty much everything (except, uh, this site, but that will happen soon enough). I haven't tried out more advanced stuff like authenticating SMTP and IMAP sessions using X.509 client certificates, but username / password authentication works well, and so long as it's wrapped inside a TLS session, I'm happy.

I'm embarrassed to admit that I had to use Google to find out how to view folders in threaded format. Damn, maybe I am lazy after all. It's pretty easy: click on the folder, and then select "View | Organise by thread" from the menus. I'm not sure if I really like the way that Mail.app displays mail threads yet. We'll see.

Multiple identities presented another problem. There just didn't seem to be any way of doing this, but my friend Google found out how. Why didn't Apple document this feature?

As you'd expect, the system address book did an admirable job of importing several disparate address books from several sources. Thunderbird can be very stupid about address book entries, adding new entries for case changes, but AddressBook.app sucked it all in and made sense of the lot. Will my phone take a couple of hundred more email addresses, I wonder?

Would it do custom headers? Not by default, but the preferences system was likely to have some form of knob somewhere. Sure enough Google came up with a page describing exactly how to do this. Cricket from the Mail development team wrote an AppleScript to do all the magic, but to be honest, it's as easy on the command line:

defaults write com.apple.mail UserHeaders '{"X-Header1", "Value"}'

This has become rather important in Ireland lately because of a recent Statutory Instrument (a law by decree of a minister), declaring that all company emails must include certain details about the company. It also applies to web sites, but that's easier to cater for. As a side-note, I had an interesting chat with a person in the ODCE about this. Not being a completely un-nerdy type, I put the case that the header of an email was a suitable location, hence the requirement for customised headers. Well, it works too:

defaults write com.apple.mail UserHeaders '{ "X-Company-Info-1" = "Network Ability Limited. Registered in Ireland No. 330478.";}'

And so on for the registered address and everything else.

So Mail.app mostly works as I want it to now. One other problem cropped up, whereby a rather annoying error message popped up, saying "The message could not be saved". What on earth was that about?

Apparently, if you use Courier IMAP, it creates the Sent, Trash and Drafts folders as sub-folders of INBOX, and this means that Mail.app didn't know where to put saved, deleted and half-composed emails. It would have been really nice to get a useful error message here, but I guess not.

The fix:

Easy, huh?