Pretty Good Privacy? No, but I do use the open source version, GPG with Enigmail and Thunderbird. Only issue I had with it is that the people I email most of the time have no idea how to use certificates and keys, so its usually a waste of time.
I've used it once, and only once. It seems to embed itself in your profile, if you lose your profile you lose your data. Even if you remember your password to get into say an encrypted hard drive, it wont accept it. You cannot backup your profile files, there's more to it then that. its deep embedded somehow.
I use PGP Corp's Whole Disk Encryption and Universal Server products at work to encrypt our laptops. I can't say I've had any major problems with it. And their support has been excellent when I needed to talk to them.
My department also uses PGP Keys for encrypting sensitive files that are transmitted to some vendors, but I'm not personally involved in that.
We don't use PGP for encrypted email. We use Axway (formerly Tumbleweed) Secure Messenger for that because we wanted recipients to view their Secure Emails over HTTPS instead of us trying to get all of our contacts to use PGP Keys...the PKI concepts are just too much for most non-technical people to grasp.
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