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History Isnt Always Pretty

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Fall is about to hit here in New England. Labor Day has been and gone; the communities pools have all closed up and I have the hard roof back on my Jeep. There is a definite chill in the air when you leave the house in the morning. It sure wasn't like that when I lived in California let me tell you. But despite where you live in the world, it's often that time of year when you sit back and think about all of those things you wanted to get done this year and how little time you have left to make good the promises you made to yourself.

I think I have an interesting perspective on many things information security that comes from the fact that for the last seven years I have systematically gone from being a vendor to a purchaser: selling software or services to being a corporate security consumer in large international banks. I drift from writing code (badly) and reading Dr Dobbs to wearing smart casuals and even suits from Gieves and Hawke when I am London. It keeps me on my toes and allows me to see both sides of the coin or at least empathize with both parties. It has also made me more than a little grumpy at times with both sides of the fence but more of that later in the year.

When we think about security management many of us immediately start thinking about policy and procedures and dusty documents usually written for the authors themselves. When I think about web security management I think about the art and science of solving real world security problems strategically.

The OWASP Bank has an SSL issue

So let's take a brief look at a problem the fictitious "OWASP Bank" has with SSL. Why pick SSL as the example? Well it's the lowest common security denominator of most web sites and when you scratch beneath the surface you will find that the majority of sites still have a significant way to go with their SSL implementations. I believe it's a management issue; a combination of a lack of awareness, education, technology, policy and process. Besides, it will prove my point that with a little thought, solving security problems strategically is very achievable and it will magically make my creative title make sense.

As CSO of the OWASP Bank I often get internal memos from compliance. They don't like email and besides now Sarbanes Oxley is, stop. Don't go there yet. Any how, a tech savvy customer recently pointed out in a letter to the CEO that we make a claim in our online security policy that we protect customers data by supporting 128 bit SSL and that in actual fact he used a 40 bit browser to connect to our site and transfer money. How could this be they asked and attached an official looking document from the Office of the Controller of the Currency stating that all data should be protected by "...equivalent to 128 bit SSL..." As I file the memo in the "to do" tray, the phone rings and it's a legal admin inviting me to a meeting about the issue next Monday. The wild fire has started and before long I know people will be talking behind my back about "another information security failure" and how "the security department is out of touch with real world problems".

I download the latest copy of Mozilla, set the cryptography to only allow 40 bit SSL and login. For giggles I turn off SSL 3.0 and 2.0 and login with SSL 1.0 and 40 bits. Really where is the problem I ask myself. I think I know the answer but call in two of my esteemed colleagues who will at some point be tasked with dealing with the issue. Jack is my technical specialist, a keen developer with an unhealthy interest in cryptography, Dilbert cartoons and Anna Kornikova. She's one step away from Julio Englesias now I have told him on many occasions but it seems to fly over his head. Maybe I am too old. I explain the issue, show him my demonstration and ask him what he thinks.

"Holly smoke, that"s not good" said Jack. "40 bits crypto can be broken in two and a half hours, this is bad. I think you need to call the CIO . Man how did that happen, John uses WebInvesitgator every week and it never said anything. I check the reports. We need to run the Security Wizard on IIS to only allow 128 bit sessions straight away." Not surprisingly Jack immediately saw the issue as a technical one and looked for reasons why it happened and how to fix it.

Jack left with instructions not to do anything and in came Hana. As a former internal auditor she is responsible for the banks security policy. Having explained the issue and after showing her my demo she sighed. "Our online policy says we support 128 bit SSL to protect all data to and from the bank; I wrote it" she explained.

So what do I the CSO think? Is it a policy violation or is it a technical issue? Or is it a web security management issue? Of course it is. Before we move on to discuss a real world solution to this trivial problem lets look some other facts that neither Jack or Hana asked.

  • Do we have any customers from International locations that need 40 bits?
  • What other regulatory bodies have standards for SSL?
  • What are the system requirements?
  • How many users stay online for more than 2 and an a half hours anyway?

Monday came around fast. In a room full of people shuffling papers and sending Blackberry messages, the legal meeting kicked off abruptly. Cara the head of Compliance explains the context of the meeting and asks me the CSO to address the meeting with the facts.

"The facts are this meeting will be very short", I start. A few jaws drop and a few people look disappointed. "SSL is a way for our users to encrypt their transactions with us over the web. It happens seamlessly in the customer browser. That's that the padlock is at the bottom of the screen". A few lawyers nod their approval that I have a good grasp on the technical subject matter. "The OCC regulation provides a guideline that we should use 128 bit SSL with our users. We do. 128 bit SSL is the default way any user would connect to us. The technicality here is that if a user specifically wanted to connect to us with a 40 bit weaker browser we would have also supported it. Let me re-iterate that if the customer intentionally chose it were would have supported it but no modern browser would do that. It is a technicality that will be changed in the next web site release in two weeks".

The facts:

  • We say online that we "support" 128 bit SSL and we do.
  • The OCC says we should use 128 bit SSL and we do.
  • If you intentionally wanted to connect to us with a 40 bit weaker browser you could. 40 bit security is generally accepted to be strong enough for two and half hours. In the last 6 months only 5 of our 250,000 users have stayed online for more than two and a half hours. Therefore this issue could have potentially affected 0.00002 % of our user population."

However to ensure that we are cleaner than clean, we have

  • Contracted with legal counsel to update us of any regulatory obligations about SSL.
  • Created an SSL configuration policy for operations to follow.
  • Bought a tool to check the SSL we are using on a daily basis and report any deviance from policy.

And with that I suggest we all enjoy the gift of time unless anyone has any questions?" I hand Cara a copy of a draft letter to the kind gentlemen who wrote to us (who incidentally offered his resume along with the hint). I sit back, sip my Grande decaff latte and grab for my phone. With a sigh I think; another day in management paradise. Another storm in a tea cup subverted. Another scenario we have solved.


All very interesting you say but what does that have to do with being inspired living in New England? Well at this time of the year I remind myself that the same things will happen that happen this year that happened for the last one hundred years and will happen for the next one hundred years. The leaves will turn into amazing colors and eventually drop off. We will be covered in snow for three months and then it will melt and we will get some small floods. Managing a web site is much like life. If you are prepared, nothing will be a surprise. After all, why turn life into a drama?

Tips for Managing SSL

  • Understand the site requirements and how SSL works - international sites may require lower strength SSL and compatibility with older browsers. Remember the level of SSL used is the users choice. You need to define the minimum level you will accept.
  • Understand your regulatory obligations (engage with legal counsel). The OCC are just one party that defines standards.
  • Develop an SSL and digital certificate policy and configuration guidelines. This should include SSL versions, cipher suites, key lengths (tied to cipher suites), and digital certificate properties and should form part of your web security policy.
  • Build or buy technology to check your web servers on a regular basis and implement a process to ensure it happens - There are commercial SSL analysis tools on the market. Shameless plug, I built one.
  • Develop a process to ensure the results are acted upon.