How to Cheat at Managing Information Security

Posted on by Ben Rothke

How to Cheat at Managing Information Security details the adventures of an information security professional and his efforts to secure corporate networks. 

Mark Osborne doesn't like auditors. In fact, after reading this book, one gets the feeling he despises them. Perhaps he should have titled this book 'How I learned to stop worrying and hate auditors'. Of course, that is not the main theme of How to Cheat at Managing Information Security, but Osborne never hides his feeling about auditors, which is not necessarily a bad thing. In fact, the auditor jokes start in the preface, and continue throughout the book. 

The subtitle of the book is 'Straight talk from the loud-fat-bloke who protected Buckingham Palace and ran KPMG's security practice'. Essentially, the book is Osborne's reminiscence of his years in information security; including the good, the bad, and more often then not, the ugly. 

The book is written for someone looking to develop an information security program, or strengthen an existing program, to ensure that all of the critical technology areas are covered. 

The thirteen chapters of the book cover the main topics that an information security manager needs to know to do their job. The author candidly notes that this book is not the most comprehensive security book ever written, but contains most of the things a security manager needs to get their job done. The author also observes that information security is different from other disciplines in that there are many good books about disconnected subjects. The challenge is getting the breadth of knowledge across these many areas, which is quite difficult. The challenge of information security is to effectively operate across these many areas. 

Chapters 1 and 2 deal with the information security organization as a whole, and the need for information security policy. Chapter 1 details the various areas where a security group should be placed, and describes the pros and cons of each scenario. As one of the scenarios which place information security below the head of audit, Osborne notes that 'if you have any sort of life, you don't want to spend it with the auditors, I promise you'. 

Wherever the security group is placed in an organization, its ultimate success or failure is likely to be determined by its level of autonomy and independence. Unfortunately, in far too many organizations, information security is not given that liberty. It is often placed in a subservient role to groups with opposing interests. Any security group or security manager placed in such a situation should likely start working on their resume. 

The scenario is described in Practical Unix and Internet Security where author Professor Gene Spafford spells out Spaf's first principle of security administration. This principle states that 'if you have responsibility for security but have no authority to set rules or punish violators, your own role in the organization is to take the blame when something big goes wrong'. Spaf's principle is a cruel reality faced by many of those responsible for information security. 

Between those chapters and a few more auditor jokes, Osborne makes the blatantly obvious observation that wherever possible, one should eradicate single points of failure. As a corollary to this, Osborne notes that while trying to eliminate these failure points, companies will often build redundant systems. Part of their admiration for these redundant systems is the hope that this will simultaneously reduce performance bottlenecks. But these companies do not realize that the routers, firewalls and switches are not the bottleneck, rather it is the software application which is the bottleneck. 

Osborne plays the role of contrarian in chapter 8 when he asks why we need firewalls. He notes that if every database maker, operating system programmer and CRM/ERM vendor put as much effort into security as the firewall vendors do, then there would be no need for firewalls. Furthermore, if each system administrator worked as hard on security as the typical firewall administrator did, and devoted as much time to hardening their servers and laptops as they did; then centralized firewalls would likely not be needed. Given that the firewall-free reality is not happening any time soon, chapter 8 provides a lot of good information on everything you need to know about firewalls. 

Chapter 9 is about one of the most maligned security tools, the IDS. After providing an anecdote about a network manager who did not understand the fundamentals of how DHCP operates, and how he used Snort to debug the problem; Osborne provides a meaningful piece of security wisdom when he notes that IDS can help any network or security person understand network traffic. These devices can even give you information on new attacks and how they can be mitigated. But for an IDS (or any security hardware or software device for that matter) to be truly useful, a security professional needs to understand their IT infrastructure, the mechanics of networks and applications and the risks involved. Those who don't understand those three things will only be able to use these security technologies with minimal benefit. 

Overall, How to Cheat at Managing Information Security, is an informative and often entertaining introduction to information security.

Ben Rothke

Senior Information Security Manager, Tapad


data security identity management & governance

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