Giving Up on PGP
Filippo Valsorda wrote an excellent essay on why he’s giving up on PGP. I have long believed PGP to be more trouble than it is worth. It’s hard to use correctly, and easy to get wrong. More generally, e-mail is inherently difficult to secure because of all the different things we ask of it and use it for.
Valsorda has a different complaint, that its long-term secrets are an unnecessary source of risk:
But the real issues, I realized, are more subtle. I never felt confident in the security of my long-term keys. The more time passed, the more I would feel uneasy about any specific key. Yubikeys would get exposed to hotel rooms. Offline keys would sit in a far away drawer or safe. Vulnerabilities would be announced. USB devices would get plugged in.
A long-term key is as secure as the minimum common denominator of your security practices over its lifetime. It’s the weak link.
Worse, long-term key patterns, like collecting signatures and printing fingerprints on business cards, discourage practices that would otherwise be obvious hygiene: rotating keys often, having different keys for different devices, compartmentalization. Such practices actually encourage expanding the attack surface by making backups of the key.
Both he and I favor encrypted messaging, either Signal or OTR.
EDITED TO ADD (1/13): More PGP criticism.
kevinm • December 16, 2016 5:59 AM
The business card I gave you in Berlin did have a PGP key fingerprint but that is only one key of many. It is useful to have one well known stable key. Printing it there did not stop me from creating other keys for specific purposes. The real problem with any encryption is that almost nobody outside of the infosec community bothers to use it until after they are being pursued. People may have heard of PGP and so there is a better chance they would use it.