6 hard truths security pros must learn to live with

Caveat emptor: Security solutions will always fall short in addressing the fundamental flaws of securing IT systems

Nearly every company in the world has thousands of vulnerabilities that hackers can easily exploit. For anyone working in IT, this is not a bombshell announcement. It’s business as usual.

The reality is that IT invulnerability is impossible at any price. Instead, companies spend a major portion of their IT budgets on computer security defenses to prevent hackers from taking advantage of those same everyday vulnerabilities. The theory is simple: With enough layers of security, the bad guys will look elsewhere for easier targets.

It’s a dirty little secret in the industry that no computer security solution really works as well as advertised. Every “guaranteed-to-stop, advanced-security system” is doomed to failure. The promised goal shared by vendors and IT alike is nothing but a pipe dream. Our best effort is all we can do.

The following six hard truths of IT security show not only why today’s security solutions fall short but how we, as IT pros and an industry, can mitigate at least some of the inevitable fallout of imperfect security solutions.

Imperfect distribution of defenses

It’s hard to lay down an infallible defense when you can’t put your software on every device in your environment. Security solutions, by necessity, work on only a subset of platforms and versions, and this subset is always less than what the customer has. Some solutions don’t support legacy devices and operating systems. Others fail to keep up with the latest OS and devices.

If one thing can be said about today’s complex BYOD world, it’s that the job of securing the network went from tough to impossible. Forget that security vendors don’t support every platform. The base truth is that no one, not even IT, understands all the devices that are used to connect to your network. Is that a phone, slate, tablet, or subnotebook device? Does it run Windows, Linux, OS X, or a private OS no one on staff has ever heard of? Is it a physical or virtual asset? If it’s a virtual machine, will it exist tomorrow? Is it running on a corporate host or on someone’s portable device? Does it belong to us or a contractor?

Even for supported devices and platforms, device discovery and deployment are imperfect. You never get 100 percent of the devices scoped by your security solution, thanks to a myriad of issues, including network or site connectivity issues, blocked firewalls, offline assets, corrupted registries or local databases, separate security domains, and OS version changes.

Add to that the political and managerial roadblocks in what is often called the eighth layer of the OSI model. Management silos, business units, departments, and systems that get exempted by default -- even if you have a brilliant idea for securing company assets, you might not be able to deploy it.

As a result, IT security must live with the hard truth that some percentage of devices will never get the security software installed. At a bare minimum, it's important that any security solution be able to tell you which devices have successfully installed the software and which are having problems. Then you can look for commonalities and try to get the software installed on as many devices as possible.

But installing the software is only the first challenge.

Insufficient staffing for deployment and monitoring

Too often, companies buy a great computer security solution, then fail to deploy it appropriately, if they deploy it at all. Months are spent evaluating and arguing for a big security purchase that ends up languishing unboxed in a corner somewhere. Or some unfortunate, lone employee is told to deploy the new solution despite already being overloaded with mission-critical work that is considered their “real job.”

The employee puts in a hero’s effort to deploy what they can in a few days. They become a pseudo expert on the device and the threats it’s supposed to prevent. They do their best to configure the device, and for the next few days or weeks, they put in a passable job of monitoring it.

Then their other mission-critical priorities take over. Pretty soon that cool new security tool is monitored less and less. No one has time to track down false positives, much less follow up on alerts. Not long after, the device is kicking out alert after alert, all of which gets lost in the noise of other poorly monitored security devices. The Verizon Data Breach Investigations Report finds that 70 to 90 percent of all malicious incidents could have been prevented or found sooner if existing logs and alerts had been monitored. It’s little wonder given this prevalent, nearly inevitable cycle from deployment to disuse.

Computer security devices are never self-maintaining. They need the right teams, resources, and focus to even come close to their promise. Companies are great at buying capital assets, but they’re afraid to increase operational expenses and headcounts. This means built-in failure. Don’t set yourself up for it. Get a plausible staffing solution in place before you purchase any security technology.

Hackers need to find only one weakness

Suppose a company has 1,000 Web servers, and 999 of them are fully patched and perfectly configured. All a hacker has to do is fire up a vulnerability scanner and point it to the right domain name or IP address range -- game over. Scanning 1,000 computers takes only marginally longer than scanning one.

A typical vulnerability scan will bring back one or more vulnerabilities on every server, if not dozens of vulnerabilities. When the scan is finished, all the hacker needs to do is pick through the juicy results to decide where to exploit first.

This one-weak-link-and-you're-hosed maxim is nowhere more obvious than in malware campaigns via email. Send a malware-containing message to a large set of employees, and at least one person, no matter how smart, will open the email and blindly follow every suggested command. I’ve been involved in dozens of antiphishing education tests over the years, and in every case, a fairly large number -- between 25 and 50 percent -- of employees can be phished out of their credentials in the first round. While the conversion rate (as we call it) drops with each successive round of sending another test to those who have passed the prior trial, there will always be some portion of users that responds to every phishing attack.

The more complex your staffing mix becomes, the harder it is to shore up your defenses. Some of the biggest hacks in recent years have come from exploited contractors. One of the most damaging hacks, on Target retail stores in 2013, came from an exploited HVAC contractor.

Sometimes attackers can go right after your most trusted protection. In one of the most sophisticated attacks ever, an advanced hacker group compromised long-lauded computer security company RSA, using an attack centered on several pieces of old, unpatched software. Then they sent a malicious spreadsheet file, which helped them break in.

Forensics revealed that the users would have been prompted with no fewer than five messages warning that the content they were about to open could be malicious. In every warning instance, they had to choose a nondefault answer to bypass the warning, and in every case they did. Once the attackers got in, they stole the digital secrets to RSA’s much trusted SecureID key fob and used what they learned to exploit their ultimate targets, which included U.S. military giants Northrop Grumman and Lockheed-Martin. Even if you have your security down pat, attackers will exploit your business partners and use what they find against you.

Even if you’re perfect at detecting and remediating vulnerabilities, all an attacker has to do is use vulnerability analysis tools to “fingerprint” each of your operating systems and applications exposed to the Internet, then wait until one of those software vendors releases a critical patch. No matter how great a company is at patching, they aren’t likely to patch assets faster than the attacker can make use of tools available within hours of the announced vulnerability.

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