Some public key infrastructures run quietly in the background since years. They are half forgotten until the life of a signed file has come to an end – but then everything is on fire. In contrast to other seemingly important deadlines (Management needs this until XY or the world will come to an end!) this deadline really can’t be extended. The time of death is included in the signed data since a long time.

The entire security ‘ecosystem’ changes while these systems sleep in the background. Now we have Let’s Encrypt (I was late to that party), HTTPS is everywhere, and the green padlock as an indicator of a secure site is about to die.

Recently I stumbled upon a whirlwind tour of the history of PKI and SSL/TLS – covering important events in the evolution of standards and technologies, from shipping SSLv2 in Netscape Navigator 1.1 in 1995 to Chrome marking HTTP pages as ‘not secure’ in 2018. Scrolling down the list of years I could not avoid waxing nostalgic. I had written about PKI before at length before, but this time I do what the Hollywood directors of blockbusters do – I write a prequel.

I remember the first times I created a Certificate Signing Request (CSR) and submitted it to a Certificate Authority (CA). It was well before 2000, and it was an adventure!

I was a scientist turned freelance IT consultant – I went from looking at Transmission Electron Microscope images to troubleshooting why Outlook did not start on small business owners’ computers. And I was daring enough to give trainings, based on the little I knew (with hindsight) about IT and networking. I also developed some classes from scratch – creating wiki-style training material, using Microsoft FrontPage 1998.

One class was  called networking and security of the like, and it was part of a vocational retraining curriculum – to turn former factory workers and admin assistants into computer technicians. For reasons I cannot remember I included a brief explanation of the RSA algorithm in my clunky FrontPage site. It was maybe a pretext to justify an exciting lab exercise: As the PKI history timeline shows, SSL was still rather new. Press releases by Austrian IT companies highlighted the military-grade protection from eavesdropping. It felt like Star Trek. One of the early Austrian National CAs offered ‘light’ test certificates. The description of the enrollment process was targeted to business users, but it was pure geek speak: A mysterious multi-step procedure explained in hacker terms like Secure Vault.

I don’t remember if my students found it that exciting or if the test enrolling a lots of certificates simultaneously did work so well at all. But I was hooked.

As a freelancer I started working with my former colleagues again – supporting the sciencists to subvert re-interpert the central IT department’s policies by setting up their own server, or by circumventing the firewall by dialing in to their own modem. This were the days of IT hype in the late 1990s before the dotcom bust. The research center had a new CEO with an IT background, and to get your projects approved you had to tack the label virtual onto anything. So I helped with creating a Virtual Materials Science Lab – which meant we used Microsoft Netmeeting.

Despite or because of such activities I also started working for the IT department. It was the time when The Cluetrain Manifesto told us that hyperlinks were subversive. As a ‘manager’ I should have disciplined shadow IT admins purchasing their own domains and running their shadow servers, but I could not stop tinkering with the web servers myself. It was also the time when I learned that to make things work in larger organizations – or a combination of several of those – you often need to social engineer someone.

We needed a SSL certificate – and I was the super qualified person for that task, based on my experience playing with the Secure Vault. But creating and submitting the CSR, and installing the certificate was the easy part. There were unexpected challenges:

The research center had a long legal name – 65 characters including the final dot in the indication of the legal entity. Common Names in X.509 certificates are limited to 64 characters, so I could not enter the final dot in IIS’s (Internet Information Server’s) wizard for CSRs. The legal name was cross-checked against the Dun&Bradstreet database. One would think that the first 64 characters of a peculiar German name would have been sufficient, but no. It took several phone calls – and faxes! – to prove to the US-based CA company that we were who we claimed to be.

The fact I called a CA company in the US might highlight a mistake: If I recall correctly Big CA had partners in Europe already at that time, but I missed that, or I wanted to talk to the mothership for some reason.

To purchase the certificate from the US-based company you needed a credit card, to be entered exactly when you submit the CSR. This process was disrupting the usual purchasing procedures and I had to social engineer somebody from the procurement department to join me in my adventure, bringing the corporate credit card.

The research center was a company owned 51% by government – so you had SAP and insane management deadlines as well as conferences and academic publication records. The Internet in general was still dominated by its academic roots. Not long ago, there had been a single web page listing All WWW servers in Austria, and that page was run by the academic internet backbone. Domain registration data were tied to a person, to the wrong person, or to the wrong entity – which came back to bite you later.

Fortunately the domain assigned to the SSL certificate belonged to us – so I did not have to  social engineer a DNS admin this time. But it was assigned to a person and not to the organization. The person was an employee in charge of the network, but how should you prove that? More faxes and phone calls were required to sort out the fine legal points.

I did not keep records of that period, so I don’t know if this web server is alive or if at least the domain still exists. Maybe unlikely, given the rapid decay of rotting links. But while researching history for this post – randomly googling for early versions of Microsoft’s web servers – I discovered interesting things. There is a small change it may be alive!

The first version of the Windows Certificate Authority had been released as an add-on to Windows NT 4, as part of the so-called Windows NT 4 Option Pack – the same add-on that also contained the webserver (IIS) itself. It was the time when I learned ASP programming by going online via dial-up and browsing through MSDN as quick as possible not to overspend my precious monthly online time.

I wanted to relive the setup of Internet Information Server 4.0 as and the Option Pack – and found lots of support articles and how-to’s, like this one.

However, I also found live websites like this:

This is only the setup CD, so no danger yet, but you can as well find sites with the welcome page of the operating web server online – including sample ASP applications – which I don’t show deliberately. (Image credits: Microsoft.)

I wonder why I had been frantically re-developing my websites in ASP.NET from scratch – ‘just because’ ASP was outdated technology, even though there were no known vulnerabilities and the sites were running on a modern operating system.

Time to quote from Peter Gutmann’s book Engineering Security:

A great many of today’s security technologies are “secure” only because no-one has ever bothered attacking them.

… which is also true for yesterday’s technology still online!