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.encryption, mail.app, Apple Mail, usability, user friendly, certificates, Thawte, just too bloody difficult

The Hawk Wings’ Plugin and Addon List gets five new entries this week:

• Address Book Reports (smarter printing of Address Book info) was added to the Address Book Section.
• Whereabouts (sharing Address Book contacts over the Internet) was added to the Address Book Section as well.
• Chibi Ninja (cross-platform encryption for emails in Apple Mail) was added to the Added Functionality Section.
• An AppleScript that will automatically reply to requests for read receipts was also listed in the Added Functionality Section.
• iVoiceMail (voice recordings in Mail.app messages) finds a home in the Added Functionality Section as well.

That makes 108 plugins, addons, helpful apps and AppleScripts to make your Mail.app experience quicker, smarter, broader and more enjoyable.

This week Hawk Wings also got Recent Comments in the sidebar so that you can more easily benefit from the experience of others with these addons. It got some advertising.

Hawk Wings also passed the million mark this week. It has now served 1,098,154 pages. w00t! ;-)

Ever wanted to send an encrypted message in an email but haven’t wanted the trouble or difficulty of obtaining a digital certificate?

Chibi Ninja, a new app released yesterday, might be for you. It allows you send an encrypted message (and image if you want) through Apple Mail which the recipient can decode using the same password you encrypted it with.

When you launch the app you are presented with its decryption window:

This offers you the choice of one of four encryption standards or ciphers — blowfish 128 bits, cast 128 bits, desx, 192 bits or rc5, 128 bits — for the message and a box to enter your chosen password.

Clicking the Chibi Ninja Mail button opens a message editor in which you compose the message. It allows you to add one image to the message, and to compose mixed messages in English and one other language (currently it supports Bulgarian, Chinese, Greek, Japanese, Korean, Polish, Russian, Simplified Chinese, Thai, Turkish, and Ukrainian).

You can also enter a comment to accompany the message that will not be encrypted and auto-generate a password for the message. You will need to send the password that you choose to the recipient. The developer suggests by phone or by hand.

When finished, clicking the editor’s “Create Mail” button launches the encrypted message in a Mail.app email:

Send it and then the recipient can copy the encrypted part to their clipboard, launch Chibi Ninja, enter the password that you sent them and decrypt the message.

Chibi Ninja is cross-platform, which means that this process will work for messasges received on any kind of computer.

Chibi Ninja is freeware (donations not refused) and is available from the developer’s web site.

EnScrypt is a series of AppleScript modules that offer encryption for emails and text.

Using the “Blowfish” 128-bit encryption algorithm, it can encrypt Apple Mail messages, TextEdit or Word files, with the promises of support to come for more apps and file formats.

It also includes the SHA1 algorithm for digital signatures and comes in the form of a stand-alone app with its own installer.

EnScrypt is free and available from the developer’s web site.

GPGMail is a plug-in that enables the sending and receiving of encrypted emails in Apple Mail. It works in Tiger and Panther, and acts as a front-end to macgpg, the Mac port of an open source encryption engine, gpg. You will need to install macgpg first.

After installing GPGMail, you will find a new sub-menu under the Message menu, from which you can manage your digital signatures and other encryption options. The developer’s website provides a list of the plug-in’s limitations, including the fact that encrypted messages are just stored by Apple Mail and not indexed.

It is freeware and is available from the developer’s website.

Joar Winfors provides some background on his site about using digital signatures in Apple Mail.

UPDATE: GPGMail 1.1.2 released, 5 February 2006.

UPDATE: 25 July 2011 The GPGTools web site now hosts this plug-in.