PGP For Intel Macs

PGP just released a beta version of PGP 9.5 that has universal binary support. I used to use PGP back in the day on Windows, but didn’t really keep up with it, eventually moving on to GnuPG for my encryption needs. However, after seeing the note about this new release, I thought I’d give them another shot. I always loved their nice key management (something GnuPG doesn’t have a great front end for at the moment.)

I was browsing through their user’s manual while downloading, and came across a paragraph titled “Memory Static Ion Migration Protection” in the “Special Security Precautions Taken by PGP Desktop ” section. This thing goes on about how an attacker could theoretically retrieve key or passphrase information from your machines memory – after it’s already been turned off – by reading the static charge left over from memory that has had the same information stored for long periods. This is some deep stuff here, and they go on about how they help to protect you against this remotest of possibilities. Cool stuff.

So the download finishes, and I install the thing, import my keys from GnuGP, and go to send an email, and realize that they’ve done away with the plugin model for mail, instead relying on a network proxy that intercepts mail and encrypts and decrypts it automatically, based on rules you set up. This works similarly to their Universal Server product. So now Mail.app (and any other mail client) sends mail to the proxy, where PGP will encrypt it. On the other side of things, incoming encrypted mail is automagically decrypted and then handed to the email client. Works OK (though with some pain trying to get everything set right.)

Then I realized that all the encrypted and signed email that I’d be receiving, would now be stored in PLAINTEXT in my freaking email folders, on a public IMAP server. In addition, there doesn’t even seem to be a way to turn this off or any alternate mechanism aside from not using the email proxy portion of the product. This breaks about 90% of the functionality that I use PGP for.

Without storing the encrypted/signed version of incoming mail, I can no longer guarantee that someone hasn’t messed with it on the server. All that’s left is some text pasted at the top of the mail that says it was signed and verified at some point. No indication of what that may have been, of course. At that point, someone could just as easily change the contents to whatever they like, completely bypassing any security that at one time existed.

This also goes for sent mail – it’s no longer stored in your sent folder encrypted – it’s sitting there in plaintext too. Still worse, there’s no indication of what you did to the email when you sent it. Did I encrypt it? Sign it? Who knows now – that information is gone now that we’re not storing the encrypted/signed copy of the message.

And still worse, someone could easily – MUCH TOO EASILY – forge a message that now looks like it’s been verified by the proxy, when it has, in fact, done no such thing.

They do still have a legacy mail plugin that permits decryption of older emails that you may have received and didn’t pass through the digestive tract of their new product. But get this – on the message boards someone was complaining that the plugin didn’t successfully decrypt messages from certain people. The response? “Oh, that plugin only works with some message types. Use the proxy.”

What a junker.

Yes, they protect you from some arcane attack that requires an electron microscope and a clean room to make work, but they’ll happily decrypt and store your email in the most unsafe way possible. What in the world were they thinking? This isn’t even limited to the new Mac product apparently – this is an across the board product line change that screws everyone.