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After my initial report on OS X.3 aka the Panther [Riiight, while I like the cat names I hate the whole marketing pitch Apple places them into these days, along with that ridiculous 'Mac OS X 10.3 Panther' official naming scheme... I like calling it X.3 and only put in the Panther for Google and Feedster related vanity reasons.] I found more information on the new signing and encryption features in X.3's Mail application.

Mail icon My conclusion was, and still is, that apart from the hassle of getting a certificate, this is quite a sleek and neat way of improving e-mail. By now I have collected a few experiences with the new feature.

The good news is: If the people you send messages to are using Mail as well, things are ultra-smooth. Things are very unintrusive and Mail 'just works' as you'd want it to without a single bit of hassle. Dave finds this impressive – I think that's the way software ought to be and Dave's enthusiasm is caused by the poor quality of most software.

Once you leave the realm of your intelligent, hip and good-looking friends, you'll be dealing with people who won't appreciate your signed messages. Some of them will even ask you what the attachment is that's enclosed in your e-mails. That's where the technical bits of the magic start to be visible and potentially ugly.

The signature Mail generates is sent with the message as an attachment. While X.3's Mail will automatically interpret this attachment, people not enjoying that application may be confused (and disappointed possibly – seeing that simply double clicking it won't even give you the joy of a virus). Hence, it's probably advisable to not send signed messages to people who won't appreciate them.

That's where an obvious suggestion for improvement can be made: Right now, Mail only remembers the latest the latest state of the 'Sign' and 'Encrypt' options. Doing so for each recipient would make things much smoother as you – me at least – will find constantly thinking about other people's e-mail clients' and toggling those switches accordingly a bit annoying. The system's address book is versatile and extendible enough to simply store the signing/encrypting information along with the contact information. Doing this wouldn't be too tricky.

Of course Mail could even be smarter and check the e-mail clients of your incoming messages and suggest to activate signing messages for those senders who are in your address book and use a client capable of dealing with signatures. – Just a thought that came to my mind, I'm not sure whether having this amount of 'cleverness' will actually be a good idea and work well enough to not be annyoing.

A little annoyance I saw when receiving signed messages is that when displaying them, Mail seems to ignore the PreferPlainText user default. That default is essential for my sanity as it tells Mail to ignore the HTML parts of messages. I hope that Apple will fix this but I am not too optimistic as this is a hidden preference. Hence I am not sure whether filing a bug report will be a good idea. – Perhaps they'll simply 'fix' the problem by removing the feature...

A final problem I see is for people who don't always read their e-mail on their Powerbooks but have to use other peoples' computers or even web mail which doesn't support any of those features (does Apple's iTools e-mail?). For those people receiving encrypted messages may be a bit annoying...

I don't think these problems are a big deal right now – the main problem remains the hassle associated with getting yourself a certificate to use in the first place. Perhaps adding those features to Mail is a move for the future. Should signing and encrypting messages become widely spread in a few years – Apple's Mail will be ready for it. Many people and probably even more businesses should appreciate it.

Bag of links on the topic: Getting certificates, Apple tech not 25555, my first steps, installing custom CA keys, E-mail style guide.

November 7, 2003, 0:12

Trackback

Trackback “Deep inside mail.app” from fscklog:

Details zu mail.app 1.3 aus Ken Bereskins Panther Weblog (bereits hier erwähnt): Einmal die Möglichkeit endlich in der Inbox das kleine Reply Icon verwenden zu können, um dann wirklich seine entsprechende Antwortmail nochmals angezeigt zu bekommen. …

November 8, 2003, 19:50

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