What Happened When a PGP Desktop User Upgraded to Leopard

If you are using Tiger and PGP Desktop, you may be on the brink of disaster so read on.

I’ll merely describe what happened to me so this is not fantasy.

Let me describe where I was first.

My personal data security is not much of a concern. However, as a media and IT consultant, I keep a lot of confidential financial data belonging to my clients. That’s what I worry about. As PGP Corporation’s PGP Desktop is the only commercially supported and reasonably priced alternative I know, I’ve kept my data secured in the following ways:

  • PGP Disk: As a locked-up repository of large amounts of confidential data.
  • E-mails secured with PGP’s mail bundle: A few of my clients prefer to send me PGP encrypted data only. My whole comms with them are archived in this way.
  • PGP encrypted individual files. That’s where I store my passwords for example.
  • Pretty damning, huh? Indeed. And imagine losing access to part or even whole of that data.

    Indeed that’s what happened when I upgraded to Leopard. (Of course I first made a bootable backup of my Tiger system using SuperDuper.) So in a way I’m always safe. Whatever working condition my system is, if Leopard does not work for me, I can at least boot back to Tiger from an external firewire disk and rescue my data.

    As soon as I installed Leopard, I tried the latest PGP Desktop I have: 9.5. (I had lost hope of 9.6 because PGP disabled the vital mail bundle in 9.6 – without any prior warning!)

    App itself: When I tried firing it up, nothing happened. The app seemed to be launching and then disappearing to oblivion. This app certainly was not going to work.

    Disk: Tried to mount my current PGP Disk, same failure.

    Mails: Since there was no mail bundle anymore, I had no way of accessing thousands of locked e-mails.

    My passwords on PGP encrypted file. As I could not fire up PGP Desktop, that was a lost cause too.

    Can you imagine the shock and anger?

    Leopard was fantastic and I was being kept away from it for the sake of one badly done and badly supported application.

    In the name of being fair, I must say I sustained my PGP communication still with the help of PGP. Now hold your breath: This is both exciting and useful: I fished in my hard disk for the oldest PGP Desktop I’ve ever bought: 8.1. Yes, it worked albeit partially. At least I was able to install it, import my keys, and use it to decrypt and encrypt text files!

    So if you happen to have switched to Leopard and feeling miserable as I did, you might hunt for an 8.1 to relieve your pain partially.

    I remain puzzled that 8.1 would work on OS X 10.5 but 9.6 would not. What’re the PGP Corporation guys smoking?

    If you haven’t switched yet, please move on to the next few posts as you’ll find useful information to save you from a lot of headaches – and hopefully from PGP too.

    Also, I always keep a working PC complete with the latest PGP always by my side. Yes, dear PGP Corporation. I need you so much that I keep paying double every year for your software. I can almost visualize you rushing to your customer database to search for those buyers who regularly bought both versions Mac and PC. Don’t worry, I don’t buy them on behalf of the same client. Never.


    1 Response to “What Happened When a PGP Desktop User Upgraded to Leopard”

    1. 1 Pelle Neksor December 22, 2007 at 8:22 pm

      I installed PGP 2 years ago on my PowerBook, this year I bought an Intel machine. Oeps sorry please upgrade. Now I’ve installed Leopard and I need to upgrade again.

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