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Bug Report Friday: Encryption Preferences in Mail

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I’m not sure how well this Bug Report Friday scheme is going. There are not that many entries to the corresponding delicious tag. So should it just be scrapped?

Well, I’ll stick to it this week once more. And touch the topic of Mail again. Indeed, I’m pretty sure a whole bug reporter could be filled with Mail bugs. It’s not that the application is all that bad. But there are terribly many glitches. And Apple hardly ever fixed one of them. Instead they kept doing new stuff, from giving us demented unique keyboard equivalents in German, to a new input/rendering setup to scrapping the nice mailbox drawer to completely changing the way messages are stored. And at least in my opinion only the very last of these changes was an improvement.

Encryption and signing buttons in Mail's composition window Anyway – today I have another bug which is related to Mail’s cryptography features. You’ll only be able to see it if you have a certificate installed for one of your e-mail accounts. If you have a certificate for your account, Mail will give you two extra buttons in the message composition window. One for signing your message and the other for encrypting it if you happen to have a public certificate for the messages recipients.

And your choice of whether or not your want to sign and encrypt messages is stored as a preference. While that’s a good idea, it’s not good enough. Signing a message technically means that an attachment with the signature will be added to the message. While applications that can deal with signed messages will interpret this as intended all other e-mail clients or web mail services will just display it as an attachment. An attachment with a strange file name, an attachment that makes the more ‘careful’ Windows users think you might be sending viruses and so on.

So at the end of the day, rather than having to answer ‘dumb’ questions of those who don’t know better, you’d rather not send them signed messages to begin with to avoid confusion. And that’s where having the global preferences isn’t good enough. As things are you have to keep an eye on the signature button for each message you write as it will always have the status you set for the previous message you wrote. And when you’re sending a many messages to many different people, things tend to go wrong occasionally, so you might be inclined to just stop using the signing feature at all to avoid those troubles. Which in turn means that having global preferences potentially spoils the whole feature. And from discussions with other users I have learned that I’m not alone with thinking that this shortcoming of Mail

But as I just outlined, whether you want to add the signature or not isn’t a global choice but depends on the recipient. So it’d make a lot of sense to save the preference for whether you want to sign a message or not on a per-e-mail address or per contact basis rather than globally. (#4300959)

October 14, 2005, 23:59

Tagged as bug.

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