OS X Lion and PGP

Another OS X version, another disappointment with PGP. Quick answer to your questions: PGP does not work under OS X Lion. As we speak, there is no official message on when it will. Those of us who braved the OS upgrade saw the following:

What else did you expect?

GPG Tools page says everything except the Mail plug-in works well.

So, if you get to know anything on file and message encryption in the new world of Lion, please drop a comment on this message.

Solution for PGP Desktop for Mac Mail Bundle and Snow Leopard

I’ll describe a simple workaround that may eliminate the need for the Mail Bundle forever.

I’m assuming that PGP Desktop is already installed in your system. I merely upgraded my Leopard to Snow Leopard and PGP Desktop is working fine save for the occasional non-critical crash.

The important part is to define PGP’s Encrypt and Decrypt-Verify commands as system-wide services. The Services menu is cumbersome to use but thanks to Snow Leopard, once you define a system-wide service, it pops up in the contextual menu when you right click.

For this to work, there are two important notes:
– You need to be in a text window.
– You need to be operating on editable text.

In Mail.app, when you want to Encrypt a message, just type it normally, then do a Select All. Right click to reveal the contextual menu and select Encrypt. Your message is ready to go, properly encrypted by PGP.

Decrypting received messages is just a little more tricky but you’ll get used to it in no time. The problem is the message does not contain editable text. Just hit reply to open a new message containing the received text. Of course this gives you the received text in an editable window. Now do a Select All and then right click to reveal the contextual menu, and finally select Decrypt-Verify. Now you have the original received message properly Decrypted. If you want to reply it at that point, write your reply and Encrypt as above. If you just want to read it and reply later, just discard the message window that contains the decrypted text.

It’s really easy and I see it no different that the routine with the Mail Bundle.

And now the mother of all tips: Since we’re talking of a system-wide service, the routine above works exactly the same using any web mail system be it Gmail, MobileMe or anything else.


Postscript: Of course PGP Corporation could have given us something like this at exactly the time that they said “Don’t upgrade to Snow Leopard!” If, of course, they had been anything like a decent customer service company. It’s almost farcical to think that they should have banned me from PGP customer forums. I’m their best ally in the blogosphere trying to help PGP Desktop Mac users!

This is how your Services menu should look like.

This is how your Services menu should look like.

Thus you write your message and encrypt it. Once you manage to get Encrypt and Decrypt-Verify services in your contextual menu, happiness could not be far behind.

Thus you write your message and encrypt it. Once you manage to get Encrypt and Decrypt-Verify services in your contextual menu, happiness could not be far behind.

Hope for mail bundle users

If you are, like me, in need to encrypting your Mail.app communication, there is hope. While PGP Desktop no longer functions and there is no clear timeline for when it ever might, it appears text file encryption and decryption works.

While it’s not quite the same as the convenience of the Mail Bundle, you can just use TextEdit to create a new plain text file and then encrypt it via the services menu. Then just paste the text into your mail message. The reverse of the procedure is valid too when you want to decrypt someone else’s message.

Just tested. It’s working fine.

Rick Forno: WTF

Rick Forno has said it better than I ever could. So allow me to elevate his comment to a post.

(sent out to my mailing list this evening)

Snow Leopard comes out for OSX users today. OSX 10.6. Hurray!

While watching the Redskins-Patriots on the big screen, I go about trying to upgrade my test laptop only to discover the Apple DVD is not recognizing the hard drive as something that can support OSX. WTFO? Resourceful as ever, I begin to Google for answers.

As I Google, an email[1] arrives from PGP.COM saying that their current product is incompatible with 10.6 and if users want to use PGP they should not upgrade but that if we “intend to upgrade to Snow Leopard, you must decrypt all PGP encrypted drives and uninstall PGP Desktop before upgrading the system to Mac OS X 10.6.” They go on to say that 10.6 support is forthcoming in their next major release but offer no details on when it will be, except to say they’re accepting beta applications now.


Taking beta applications now? There are freeware and shareware developers whose products are fully compatible with 10.6 and PGP only now is soliciting beta testers? Did the company just realize that OSX 10.6 was coming out today? Didn’t they get the memo? Are there no OSX users at PGP Headquarters?

So back to my stalled Snow Leopard upgrade to my laptop: Thanks to Google’s timely archiving of the Apple support boards[2] I found out that not only did I have to uninstall PGP, repair disk permissions, and reboot, but since PGP apparently does something to the OSX partition table, I had to enter Disk Utility and dynamically resize my laptop’s hard drive a few megabytes in size just so a new partition table could be written — at which point I was able to install OSX 10.6 just fine. (Note that I had installed, but did not use, PGP on this computer, and certainly did not use their Whole Disk Encryption.) What kind of stuff did PGP have to write to my partition table to make it unreadable by Apple’s own installation disk? Scary!

Unfortunately, after many years of dealing with their quirky product registration system and hiccups with routine OS upgrades, I am forced to say that PGP has lost me as a customer — their tolerable corporate quirks aside, I cannot trust any security product that tweaks (nay, borks) my system in such a troublesome manner and certainly one that seems to treat Mac users as third-class citizens.[4] I’m not the only one who feels this way, either — indeed they are correct in titling their concerns the Audacity of Hopelessness.[3]

I will follow the lead of my coworkers and other securtygeeks and embrace GPG instead.


[1] http://blog.pgp.com/index.php/2009/08/sneak-peek-pgp-whole-disk-encryption-for-snow-leopard/
[2] http://discussions.apple.com/thread.jspa?messageID=10063151
[3] https://pgpsucks.wordpress.com/
[4] How about their officially-unsupported but unofficially-supported Mail.App plug-in? After nearly a decade of OSX in the marketplace they still don’t officially support Apple’s Mail program? WTF, indeed.

PGP: Don’t upgrade to Snow Leopard!

This must be the Audacity of Hopelessness.

PGP Corporation has just circulated a public message declaring that PGP Desktop won’t work on Snow Leopard. Hence, in all their humbleness, PGP Corporation says “.. you should NOT upgrade to Mac OS X 10.6.” (Caps theirs.)

No, they are not going to get their act together. But you the user, you do have a choice: Do not upgrade to Snow Leopard. You see, PGP Corporation is at your service like it has always been:

PGP Corporation is committed to providing Macintosh users the best possible encryption solutions and we’ve been building them since re-starting the company in 2003.

Of course.

Wait till cows come home.

We expect support for Mac OS X 10.6 to be available in the next major release of PGP® Desktop (10.0). PGP Corporation recommends waiting until PGP® Desktop 10.0 is available before upgrading to Mac OS X 10.6.

What do you mean “expect?” Really?

If you had thought that PGP Corporation would follow suit with thousands of other software developers and come up with a release that will work with Snow Leopard at approximately the same time, you had no idea how PGP Corporation works.

This is the same trusted, tried-and-tested substandard behavior from a company that should have been long wiped off the face of the market.

This company needs something beyond re-starting. Kicking, crushing, melting, decimating. Something.

Snow Leopard and PGP Desktop: So What Will It Be?

Historically, I have relied on PGP Desktop for mainly two purposes: Folder encryption and e-mail encryption. Following PGP’s massive heck-up of maintaining the software through OS updates, I gave up using folder encryption, opting instead for encrypted DMGs. Yet, for e-mail, I still rely on PGP. And I still need the Mail.app bundle that PGP clearly does not wish to sustain.

Snow Leopard brings true suspense to PGP Desktop users once again. Will the existing PGP app work under Snow Leopard? Will it need tweaks? Will it require an upgrade of the app paid/unpaid? Will it have to be a whole new release that will make all of us shell out another 150 bucks or so? I mean, really, this time it must be something like 350 bucks to hurt real bad.


With two days to go before the release of Snow Leopard, nothing makes my heart race like the issue of PGP Desktop.

Keep your comments and stories coming. This is promising to be another ‘interesting’ epoch; in the sense of the Chinese curse “May you live in interesting times.”

Mac OS X 10.5.8 and PGP – You may upgrade, but…

Fear not. You may upgrade to what is probably the last point update of Leopard and hope that your PGP Desktop for Mac will continue to work. Tried and tested. As usual, there are few issues with disk or file encryption and the thing to watch is the Mail bundle. I’m using PGP Desktop 9.9.0 and not willing to do any updates before Snow Leopard. This combination is working well, so far so good.

The only glitch is Mail bundle seems to be unable to invoke PGP from time to time. So I’d select to encrypt a message and then hit send, nothing happens. No trace of the message anywhere in Sent or Draft, anywhere. Problem is easy to address. Just launch the PGP app and Mail now knows how to handle your encryption requirements. This has been going on in an erratic way.

Having mentioned Snow Leopard, let’s hope that PGP does not mess things up. Many of us do want to keep working the way we have always worked: With a bundle that ties with Mail.app. If it does not, this will probably be it for me and I’ll switch to open source.


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