In a widely known and notorious study called “Why Johnny can’t encrypt”, a series of volunteers were asked to step through a sequence of tasks using PGP 5.0, then considered to be a good example of well designed security software. Quoting from the introduction of the paper:

The analysis found a number of user interface design flaws that may contribute to security failures, and the user test demonstrated that when our test participants were given 90 minutes in which to sign and encrypt a message using PGP 5.0, the majority of them were unable to do so successfully.

Given that PGP’s marketing literature at the time emphasised the effort that had gone into its design, you’d think this embarrassing study would have prompted serious reform. But you’d be wrong. In a followup study in 2006 called “Why Johnny still can’t encrypt”, researchers discovered that PGP 9.0, despite many changes from version 5.0, still confused people:

We found that key verification and signing is still severely lacking, such that no user was able to successfully verify their keys. Similar to PGP 5, users had difficulty with signing keys. Three of our users were not able to verify the validity of the key successfully and did not understand the reasoning to do so. Four users were not able to sign the key, these users attempted to but struggled with the interface. They did not understand that in order to ‘verify,’ they must ‘sign’ the key rather than just click ‘verify’ ….. Digital signing of messages is more problematic in PGP 9 than PGP 5 as none of the users were able to sign messages using PGP 9

During the early ‘90s the so-called crypto wars raged between governments and mathematicians. Governments feared a new era of unreadable communications and the crime it would enable. Cryptographers feared government overreach and surveillance. History records that cryptographers won the crypto wars and eventually the FBI accepted the new world order.

But did governments really lose? Or did they simply lose interest?

At a talk in 2012, investigative journalist Duncan Campbell discussed a series of successful terrorism prosecutions and how encryption had been used:

The hijackers who attacked New York and Washington did not use encryption at all. On the 18th of September 2001, FBI Assistant Director Ronald L. Dick, who was head of the U.S. National Infrastructure Protection Center, told reporters at an FBI briefing that records of the Internet messages between the 19 hijackers had not involved any encryption or concealment. He said it was simple e-mails back and forth. That was it: no encryption. A decade of fear, the biggest plot ever, the biggest loss of life — no encryption. And exactly the same conclusion was reached in the large official 9/11 report (see image). The hijackers had used regular e-mail services like Hotmail, they’d been taught to use simple codebook substitutions, such as calling the White House “The Faculty of Politics”, or the World Trade Center “The Faculty of Commerce”. They did not encrypt.

Campbell goes on to study over 10 more terrorism cases. PGP surfaces in only one of them, a case that involved cybercrime in aid of terrorist fundraising. So perhaps a more accurate interpretation of history is that governments simply stopped caring when it became clear just how terrible the cryptographer’s software really was. The Big Fear was that terrorists would encrypt their communications and become invisible to the authorities. That fear receded when it became apparent that PGP was so bad terrorists would literally rather die than use it.