The frustrations of encrypted mail in Mail.app
Matt Haughey (his wikipedia entry 
kewl!) has written a great piece on the frustrations of trying to set up and use encryption in Mail.app.
He suggests that,
Encryption seems to lie somewhere between privacy, security, and a mountain of engineering acronyms and standards. Unfortunately for regular people, most of these systems are overbuilt and the process is so painful that I would argue it barely even functions.
He describes his experience of following Joar Winfor’s excellent tutorial on setting up encryption in Apple Mail, drawing attention to the frustrations of the whole process.
He also makes a few suggestions on how some usability could be introduced. A great read.
Tags: Apple Mail, certificates, encryption, just too bloody difficult, mail.app, thawte, usability, user friendlyRelated posts
February 5th, 2006 at 2:08 am
Dear Sir:
Is possible for you viste this site:
https://sce.ctt.pt/site/base/usermanual_macos.html
and give your opinion, please ?
Yes, this is in portuguese language, but … one ideia.
This is not spam. Is a effort. Workinh many, many hours gratis. without money.
Is for mac users in Portugal have same chances that user windows. The lawyers first, everybody more late.
This email for this site is to request help for develop the aplication -plugin MDDE -because unhappyly the Apple in Portugal does not exist.
Exist any person of the Apple to help us, please ?
Make conection whit enginers or programmers or others for help technique.
This is for Apple develop the market. Users whit options (if one aplication exist for Mac) is a potential purchaser of MAC.
Sorry, my englis is bad. The Sherlock ins`t perfect, still.
Best Regards
Manuel Silva Manuel Joaquim Marques da Silva
A?ɬßores
Portugal
mail: manueljoaquimsilva@mail.telepac.pt
Portugese MAC User.
February 5th, 2006 at 2:21 am
Manuel wrote:
I visited the site but my impression was that all the documentation was in Portuguese. That is going to be a barrier for many.
I think that the Apple in Portugal does exist. There is an excellent Apple blog run by a Portugese Mac developer.
February 5th, 2006 at 3:51 am
Dear Tim and readrs:
The Apple in Portugal is independent reseller.
Yes is difficult for the readers learn portuguese, but is possible download the application and the screenshot help, give a opinion.
I posted one commentary in http://don.yacktman.org/blog/. He understand the portuguese language.
The Portuguese bloguer is
http://the.taoofmac.com/space/ ?
Best regards
Manuel Silva
February 5th, 2006 at 10:34 am
Don speaks Portuguese? He’s full of surprises!
Yes, The Tao of Mac was the blog I was thinking of.
I”m not a developer myself, so I can’t really help you, but I wish you well in the development of your plugin!
Tim.
April 28th, 2006 at 12:34 am
Apple has taken one step for .Mac users that makes encryption easier: .Mac users are now showing up in my Address book with certificates, making it easy to send signed mail from my .Mac address and to exchange encrypted messages with other .Mac mail correspondents. I’m not sure how they’re handling the certificate exchange, but my keychain has a certificate for my .Mac mail account, and certificates for several of the @mac.com people with whom I communicate. It just works. The .Mac site is silent about this great feature.
Apple appears to be the trusted certificate authority issuing the certificates.
April 28th, 2006 at 12:40 am
Hi Gibbons. I’ve tried to cover this here - http://www.hawkwings.net/2005/11/28/use-your-ichat-certificate-to-sign-mailapp-emails/ - but as you say, it is seems to be little known.
April 28th, 2006 at 12:47 am
Thanks Tim - I must have seen this item on your site because that setting is enabled on my machine. Apple would do well to turn that on by default - it’s a great feature, and adds value to the .Mac service.
April 28th, 2006 at 12:54 am
I sometimes have problems when I send signed emails to people who don’t understand what the S/MIME attachments are. It’s worse when their email clients don’t understand them. A fellow sent me an email the other day saying “Did you send me a message yesterday? I got a security warning about it so I didn’t open it.” He’s using Microsoft Outlook Express as his mail client.
It Would Be Greatâ„¢ if you could store mail security preferences in your Address Book for each potential recipient, so that for person A, mail will always be sent encrypted, person B will always get signed mails, and person C will get no special treatment. Right now Mail sets its signing/encrypting setting based on the last mail you sent.
April 28th, 2006 at 1:01 am
That would be great. I guess that Apple has held off doing this partly because encryption is not widely used. Which is, of course, a bit of a Catch 22 situation!