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PGP with Snow Leopard ?

All,

I currently use GPGMail ( http://www.sente.ch/software/GPGMail/English.lproj/GPGMail.html) for signing and encrypting my e-mail, but from what I've read, the author has no current intention to port this to Snow Leopard.

Can anyone recommend an alternative solution for encrypting, reading encrypted messages and signing / verifying signatures with Mail.app ?

If not, could anyone recommend another mail client with the following features:
- Solid IMAP support and offline caching
- PGP / GnuPG support
- Support for random signatures
- Support for multiple mail accounts

Posted on Aug 31, 2009 12:50 AM

Reply
109 replies

Sep 10, 2009 12:03 PM in response to John Lockwood

John Lockwood wrote:
Everyone seems fixated on GPGMail, as I pointed out PGP.com have confirmed they will be updating their product for Snow Leopard Compatibility.



Aside from the excessively high cost of PGP, my understanding is that PGP email uses some sort of intercepter in lieu of a plug-in, and the result is that your encrypted mail is stored in an unencrypted form on your computer after you've read it.

I could be mistaken about this, as I just learned about it from reading the PGP forums, but this would be a deal-breaker too, as it doesn't protect this data in the event of theft of your laptop, etc.

Sep 10, 2009 12:14 PM in response to dff

dff wrote:
Thanks a lot man.
Nice of you to help the community 🙂


It's no big thing - before I got a proper day job with IRC restrictions, I spent most of my time contributing to the Linux kernel and Apache. These days most of my time is going into my iPhone app, but since I've lost a week due to a dead MBP (although Apple are being awesome about the repair) I've lost momentum on that 🙂

Sep 10, 2009 12:15 PM in response to John Lockwood

John Lockwood wrote:
Everyone seems fixated on GPGMail, as I pointed out PGP.com have confirmed they will be updating their product for Snow Leopard Compatibility.


MacGPG is a better product and being Open Source at least it's auditable.

More importantly, I have a GnuPG key that is known to thousands of people and signed by people who carry weight in my community - I don't want to lose that.

Sep 11, 2009 2:25 AM in response to leeb00

leeb00 wrote:
John Lockwood wrote:
Everyone seems fixated on GPGMail, as I pointed out PGP.com have confirmed they will be updating their product for Snow Leopard Compatibility.



Aside from the excessively high cost of PGP, my understanding is that PGP email uses some sort of intercepter in lieu of a plug-in, and the result is that your encrypted mail is stored in an unencrypted form on your computer after you've read it.

I could be mistaken about this, as I just learned about it from reading the PGP forums, but this would be a deal-breaker too, as it doesn't protect this data in the event of theft of your laptop, etc.

The pricing for PGP is weird and I can see why you think it is expensive and I am now confused by their pricing.

I had originally for my own needs looked at PGP Whole Disk Encryption, and PGP Desktop Professional. Desktop Professional is basically Whole Disk Encryption plus Email encryption. The difference in price of these is only £80 but the cheapest email only version is £149 (a lot more). I had expected the email only (Desktop Email) product to be cheaper than the Whole Disk Encryption only product.

Regarding how it works, certainly I have confirmed the Windows version works as an email proxy so this would support what you found and is indeed 'bad'.

I also found the following in a PGP Desktop (for Mac) ReadMe

+"PGP Desktop is initially installed in Automatic mode. You may change this in the+
+Preferences if necessary to accommodate your environment. Automatic mode uses Mac OS X’s built-+
+in firewall functionality to redirect your email client connections through PGP Desktop."+

So I agree it is looking a bad solution.

Oct 6, 2009 4:04 PM in response to Matthias Stegner

I also switched to Postbox, and it does indeed run Enigmail to handle GPG messages. As the poster above said, it runs fast and is integrated with the Mac address book, unlike Thunderbird. It also run many Thunderbird add-ons, and has a much nicer folder arrangement than Apple Mail (which groups all sent together, all trash together, etc.) This makes it much easier to navigate. There are $10 discounts available right now too.

Oct 7, 2009 11:02 AM in response to John Lockwood

Indeed S/MIME is useless for PGP users.

S/MIME is also inferior in a whole wide range of areas to PGP.

I find it almost unbelievable that Apple still doesn't have built-in support for PGP, especially in view that they use PGP to sign their software!

It is indeed very sad that Apple feel free to make incompatible changes to the Mail plugin API, and even worse that they don't support third party developers in ways that would allow such missing features to be more easily added as plugins.

Indeed more users need to go to the feedback page and request full and modern support of PGP in Mail.

Oct 7, 2009 11:07 AM in response to John Lockwood

Unless PGP.com revive and fully support the Mail plugin for PGP signing and encryption then their promise to support Snow Leopard (and future releases) is pointless and futile.

The current PGP.com release is an evil application that goes behind the user's, and more importantly the system administrator's, back and offers little true support for PGP in the way that users demand.

Only proper integrated support in the MUA makes sense for decent use of PGP to form a secure e-mail environment.

PGP with Snow Leopard ?

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