Network Security, Security Strategy, Plan, Budget

Where enterprise CISOs go wrong

The best laid plans are often fraught with mistakes – some big, some more nuanced. Evan Schuman looks at where CISOs can fall short.

Enterprise security today, at least at the $4 billion annual revenue level and up, is in a precarious place. Despite GDPR and best security practices insisting on having complete global datamaps, hardly any such firms have them. Cloud use is just about universal, but the assets moving to the cloud is sharply increasing ever year. And yet, cloud security – or, more precisely, unwarranted reliance on presumed cloud security – is abysmal. 

Shadow IT is getting far worse, even though it’s been around for well more than a decade, IoT usage is soaring with security protections often barely negligible and CISO to board communications are hardly improving. Much of the board problems involve communications. But as bad as board communications are, CISO to LOB communications are widely regarded as even worse.

 Access to sensitive information is being shared more widely with all manner of partners and even some prominent customers, with woefully inadequate means to guarantee security compliance. CISOs are regarded as overly resistant to change, while some CISOs are more worried that they are being pushed to use an unproven new technology too quickly.

 As the old joke says, “Other than that, Mrs. Lincoln, how was the play?”

 The area where most security consultants expressed the greatest concern is accurate and comprehensive datamaps, aka, asset management. In short, the criticism is that hardly any large enterprises know where all of their sensitive data is, what cloud environments they control, what mobile devices exist in the company and what data those devices hold and they often have barely a clue about what applications the company is using. If security and IT don’t know where all their data is, the argument continues, how can they possibly protect it or even know if it’s been breached? Until some third-party stumbles on the stolen data in the dark web or law enforcement finds it on the server of an arrested cyberthief, these security incidents are often secrets from the very people paid to protect that data.

 “Some 100 percent of (CISOs) have apps in the cloud that they don’t even know exist,” says Gartner Research Director Sam Olyaei. That is a combination of shadow IT (employees purchasing their own cloud environments for working on their own or their business unit’s projects – without telling IT or security) and the nature of many major cloud environments, which use their own apps in addition to the ones the enterprise knows about.

Joe Nocera, a principal in cybersecurity and privacy with PwC, the consulting firm more commonly known as PricewaterhouseCoopers, agrees with Olyaei. He sees large enterprise CISOs still struggling with asset inventory. Part of that problem is that datamap perfection – knowing exactly where all data, apps and infrastructure are and what they all contain – is arguably impossible and that discourages many CISOs from seriously trying, especially when they are overwhelmed with other tasks that they can in fact master.

“They tell me, ‘I’ll never have 100 percent complete and accurate’ and I tell them ‘So strive for that 99 percent,’” Nocera says. “They are being hit by a misconfiguration or a patch to a system they didn’t even know was running on that software. They either get overwhelmed by the size and the challenge and they don’t even start or they try and do too much and they don’t accomplish anything.”

Another analyst who points to insufficient datamaps as being a key CISO mistake is Andrew Morrison, who leads strategy, defense and response for Deloitte Cyber in the U.S. Part of the negative consequences materializes with vulnerability management of applications. CISOs “are sitting on a timebomb, They can only fix or patch so many things,” Morrison says. “It’s a whack-a-mole game of patch configuration.”

PwC’s Nocera offers one solution and that is to “leverage big data techniques to better (handle) inventory and discover the environment. Any type of way to continually monitor new assets.” Some enterprises have toyed with using a modification of security’s continuous authentication to constantly watch the network for any new executables or even IoT devices – whether installed by friend or foe. Nocera says that could help with asset inventory as well, particularly when trying to identify assets or programs created via shadow IT.

CISOs “can’t depend on the rest of IT telling you,” Nocera says, adding that they also suffer from a sharp lack of resources. Also, he says, every unit is looking only for the items that most relate to their own operations. “The infrastructure team is trying to find assets, the data team is trying to discover the data, the privacy group is looking for GDPR or CCPA violations, etc.”

The challenges of asset management lead directly to the problems with the cloud, whether it’s an official cloud environment or one purchased by a renegade unit operating within the wild west rules of shadow IT.

The biggest cloud problem discussed by consultants is that many security departments assume – or, perhaps more bluntly, hope – that the major cloud environments (Amazon, Google, Microsoft, etc.) offer far more security for client tenants than they actually do.

Often, it’s not that cloud environments are necessarily less secure than the security at the enterprise tenant’s operations – although that is certainly sometimes the case – but it’s that cloud environments are working with a massive number of tenants from Fortune 1000 companies and the cloud vendor does the best it can offering a decent vanilla environment for all. But it can’t tailor its environment for the compliance and security needs of different tenant companies and it therefore assumes that every client tenant will perform their own extensive customization based on that enterprise’s security, compliance, vertical and geographic needs.

 “Cloud workflows are not inherently secure,” says Gartner’s Olyaei, who drew the comparison of a cloud tenant with a physical tenant in an apartment building. He argues that an apartment tenant has to make sure that the apartment doors and windows are locked and that no stranger is granted access, but that apartment tenant can’t control the CCTV in the lobby or make sure that the doorman and security guards stay awake and do their jobs. “The CISOs believe that it’s the (cloud service provider’s) responsibility to protect their data and apps” even though that is not the cloud company’s job, he says.

Olyaei points to Capital One’s massive cloud breach as an example of an enterprise trusting the cloud provider too much on security matters. “The fact that the misconfiguration happened is the customer’s responsibility,” he says.

Deloitte’s Morrison agrees. “In the adoption of cloud, the notion of outsourcing security responsibilities to the cloud vendor” remains, he says. Some CISOs “are learning the hard way that you’re not obviating the responsibility for security” when a cloud vendor is retained.

Morrison said some of his clients have suffered because of how a cloud vendor handled some tracking. “Things like logging and how far back they retain logs. We’ve seen a major (enterprise) have an attack and want to do the standard forensics and the data just wasn’t there because the cloud provider – courtesy of the contract – only retained that log data for 30 days,” Morrison says.

Another frequently mentioned complaint about what mistakes Fortune 1000 CISOs make today involves the fear to change. All humans fear change – and yes, despite what some CFOs believe, all CISOs are technically human – but analysts argue that this resistance to security change is proving quite counter-productive.

Shawn Fohs, the managing director of the U.S. forensic, privacy and cyber response for consulting firm Ernst & Young (EY), points to the general CISO resistance to, for example, AI’s machine learning (ML) for security, despite the fact that many of these same enterprises are aggressively using ML in other departments for research, product development or marketing analysis.

“A lot of it is a confidence issue,” he says. CISOs “have to become more aware of potential risks and how these risks are evolving. Cybersecurity professionals are hesitant to change and it’s a mistake that they are this hesitant to change.”

Much of this hesitancy to change is evidenced in purchasing patterns, Fohs said. “CISOs tend to get very focused on that we need this tool to solve this problem. They get too fixated on a specific tool and they don’t embrace all of the different tools that are available to them. They get vendor fatigue and they stick with what they know” rather than “adapting to a new mindset. They go to all of these conferences and they meet with all these vendors, but instead of actually engaging or embracing (the new tools), they just go back to tried and true. They know what has historically worked for them.” He cited continuous authentication and behavioral analyts as other examples of promising technologies that are meeting with a lot of CISO resistance.

Forrester Research Vice President and Principal Analyst Jeff Pollard agreed with Fohs and says that many “CISOs have created that situation for themselves by not being involved in innovation processes. It’s a lack of flexibility and treating everything the same. Security hasn’t been very willing to customize.” He wants to see more CISOs not only embracing DevSecOps, but taking the DevSecOps approach and applying it to improving relations with lines of business (LOB) by embedding security people within those groups.

Not only would that kind of cooperation bring security into product development far earlier, but team members would also bring back much more sophisticated understandings about the goals and priorities of those LOBs so that security wouldn’t merely improve, but could also become far more responsive to those business units and might even be able to accurately anticipate their needs.

 PwC’s Nocera also sees this complacency and lack of growth to be a key CISO mistake. CISOs “are not adapting their security model to be as agile as it could be. They are not being on the front-end of innovation. Many of these chiefs have grown up being excellent technologists, (wonderful) at responding to incidents. Their comfort zone is fighting fires,” Nocera says. 

Sometimes, good guys become bad guys with a little math error

In security circles, the typical discussion about mistakes is when CISOs/CSOs/Security Analysts are accused of making them. But sometimes it’s the cybercriminals or cyberterrorists who make mistakes. And even more interestingly, it’s sometimes good guys who make mistakes and accidentally morph into bad guys.

The recent history of security incidents gives us two superb examples of hacker mistakes turning those bold hackers into unintentional attackers.

The first is Robert Tappen Morris, who gave the industry what is arguably the very first Internet Worm (now known as the Morris Worm) back in 1988. That worm, which brought much of the Internet to a crawl or a dead-stop, was an experiment that graduate student Morris created to make a point about Internet security failings. Point made.

But his intent had never been to crash the Internet, had never been to create something that more closely resembled an early D-DOS attack than a run-of-the-mill worm. That was the result of a math error that Morris made. While leveraging holes in Finger ID, Sendmail and rsh/rexec, Morris created the worm to impact a limited number of computers globally: Just enough to make his point.

Ironically, the error grew out of Morris’ explicit attempt to make sure that the worm did not grow wildly out of control. To slow it down, it coded the worm to, in effect, ask every machine it visited whether the worm was already installed. But Morris knew that admins could simply program the system to always say “Yes, you’re already here. You can go away now.” To combat this, Morris programmed the worm to install itself even if the system said it was already there, roughly one out of seven times.

It turns out that he had intended to have it install itself either way only once out of seven times, but his math error was that he should have opted for a far smaller number. That was more than enough to crash the Internet.

 A more recent example was the Heartbleed virus, from back in 2014. In a wonderful interview with Heartbleed creator Robin Seggelmann in Autralia’s Sydney Morning Herald, Seggelmann said “”I was working on improving OpenSSL and submitted numerous bug fixes and added new features. In one of the new features, unfortunately, I missed validating a variable containing a length.” After Seggelmann submitted the code, a reviewer “apparently also didn’t notice the missing validation, so the error made its way from the development branch into the released version.” Seggelmann said the error was “quite trivial,” even though its effect wasn’t. “It was a simple programming error in a new feature, which unfortunately occurred in a security-relevant area.”

As for the impact, the Herald put it succinctly: “The bug introduced a flaw into the popular OpenSSL software, which is used by many popular social networking websites, search engines, banks, and online shopping sites to keep personal and financial data safe. It allowed those who knew of its existence to intercept usernames, passwords, credit card details and various other sensitive information from a website’s server in plain text. It also allowed for a server’s private encryption keys to be stolen.”

If the path to hell is paved with good intentions, so, too, it seems, is the path to cybersecurity disasters. At least sometimes.

Evan Schuman

I’m a Computerworld columnist and a cybersecurity writer for McKinsey. I’m also the former Editor-in-Chief of a retail IT media outlet called StorefrontBacktalk. Officially, I am the CEO of a content company called The Content Firm LLC.

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