Catch the recent “Politics, Power, and Preventative Action” podcast interview with RTJ founder Mark Mateski.

The Annoying Red Teamer: A Philosophical Approach to the Problem

Painting of Diogenes and the Lantern.Red teamers can be annoying. Sometimes the annoyance is justified, sometimes not. After all, who likes to be told that they overlooked a key assumption or failed to implement a sensible practice. It’s not surprising that many people resist even the idea of red teaming.
      As red teamers, we often lament the shortsightedness of this resistance. What we don’t discuss very often is the uncomfortable fact that we often aggravate and perpetuate it. Yes, we can be self-satisfied and snobbish. And why not? We spend our days thinking about important things other people ignore, neglect, and overlook. Even when we’re not snobbish and condescending (honest!), we have to work twice as hard not to be perceived as such. That’s just the nature of the game. Read on …

The Need for Genuine Empathy in Modern Adversarial Red Teaming

You never really understand a person until you consider things from his point of view . . . until you climb in his skin and walk around in it.”

      – Atticus Finch to Scout in Harper Lee’s To Kill a Mockingbird.

      This is the heart of adversarial red teaming, right?—to consider a problem from the adversary’s perspective. Kind of . . . what Atticus advocates is something more, something elusive, and something many red teamers unthinkingly overlook: genuine empathy. Read on …

‘Seven-Place Accuracy with Bum Data’

At times during this election season I felt as if I were living in a house of mirrors. With leaks, allegations, and counter-allegations sprouting like weeds, I wondered how, as a citizen, I could discern anything close to the truth. As red teamers, we often face a similar dilemma. Sometimes we just don’t know enough to draw actionable conclusions from the available information. Sometimes all the normative decision making approaches in our toolkit can’t compensate for the degree of uncertainty we face. Sometimes we’re forced to rely on our intuition—knowingly—while seeking new and better information. Sometimes we find opportunity in the ambiguity and uncertainty, but typically the very worst thing we can do is assert certainty where none can reasonably exist. As a Robert Heinlein character says in the short story “Space Jockey,” “What good is seven-place accuracy with bum data?”

A Red Teamer’s Take on Pentesting

pentestingPentesting can be an enormously valuable service, but we must be aware enough when hiring or employing a pentester to balance both the advantages and disadvantages of the practice. Yes, it can reveal holes in our security, but it can also promote an illusion of security. Further, while it can help validate our current security efforts, it can, if handled poorly, itself become a potential source of misperception and even vulnerability. Before opening our systems and operations to pentesters, we should consider the following caveats, cautions, and questions: Read on …

Russia, Reflexive Control, and the Subtle Art of Red Teaming

To understand the Russian approach to strategy and conflict, we must first understand something about the concept of reflexive control. Initially developed and championed by Vladimir Lefebvre, it’s a uniquely Russian view on stratagem and deception that repackages and reframes much of what we usually associate with Sun Tzu. If we expect deception and stratagem from China but not from Russia, we’ve set yourself up to be surprised. We’d be foolish to assume that the Russians are not currently employing reflexive control against the West.
      By definition, reflexive control is “a means of conveying to a partner or an opponent specially prepared information to incline him to voluntarily make the predetermined decision desired by the initiator of the action.”1 In other words, when employing the theory of reflexive control, you paint a picture of the world, that, if successful, your opponent accepts. This false picture compels your opponent to act in your favor. A close term in the U.S. lexicon is “perception management,”2 although the tone of reflexive control is arguably broader and more Machiavellian. Read on …

  1. Timothy L. Thomas, “Russia’s Reflexive Control Theory and the Military,” Journal of Slavic Military Studies, 2004, vol. 17, p. 237. []
  2. Ibid., p. 237. []

Waverley Root on ‘The Business of Democratic Journalists’

Cover200I encountered the following quote from Waverley Root last night when starting Peter Tompkins’ 1965 book The Murder of Admiral Darlan. I was unable to find the full quote on the Internet and felt obliged to post it here. I present it without excessive comment, only to note (1) how relevant it is to current debates and (2) how closely the classic concept of the intrepid journalist maps to the irrepressible spirit of the superior red teamer (bounded, of course, by appropriate rules of engagement!).

      It is the business of democratic journalists to try to turn the light of day into the dusty corners of secret diplomacy, and to expose to the view of the people the machinations which seek to dispose of them, even in the republics, in defiance of the principle which states that the people should decide their own fate.
      Such journalists are therefore engaged in an unending war against secretive officials. They seek to expose what the officials seek to hide. If they [the journalists] win, the officials of the future will be of a new stripe (of whom we have some already), who will carry on their activities in the full view of the public, hiding nothing from them.
      If the keepers of the secrets win, there will be no more journalists in the future al all, only scribes setting down slavishly what they are told to write. We have some of these already, too.1

  1. Waverley Root, as quoted in Tompkins, p. 15. []

The Roots of Red Teaming: Praemeditatio Malorum

Roots of Red TeamingOver the years, I’ve been asked my times how red teaming began. I don’t believe there’s an easy answer to the question. Some point to the German Kriegsspiel or earlier variants of battlefield simulation (chess, for example). Micah Zenko in his book Red Team highlights the Catholic practice of employing a devil’s advocate. I’ve recently encountered another example of proto-red teaming: the ancient Stoic practice of praemeditatio malorum.1 Read on …

  1. For the sake of completeness, I must note that (1) the practice wasn’t strictly limited to the Stoics, nor is Stoicism limited to the ancients. []

Informal Survey of Red Teaming Jobs

While I’ve long said that red teaming is useful for more than just security, I believe security red teaming remains by far the dominant form. To test this hypothesis, I surveyed the first five pages of red teaming jobs on Indeed.com.1
      What I learned informally confirmed my hypothesis. In the first chart, you’ll see that the only non-IT forms of red teaming that appeared were proposal management jobs and jobs that I binned in the “intelligence” category (one involved future technologies and the other described a general intelligence red teaming role). I separated the IT-security jobs—those with the red bars—into categories as best I could based on the job announcements, but the overall trend is clear: roughly 85% of the jobs listed relate directly to IT security. Read on …

  1. I used the following search string: “red team” or “red teams” or “red teaming” or “devil’s advocate” -medical -patient -treatment -nurse []