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Comfort and Risk

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My position is this: comfort with risk is one of the most essential offensive skills. Comfort with risk does not equal discomfort with caution, however. Too much discomfort with caution will not serve you in this field.

If you are going out on a mission (say to an armed facility), the risk is in going; you should remain cautious at every step, but, again, too much overt caution in the moment will have you stand out…a surefire way to get shot (no pun intended). For the rest of the operations and engagements you go on, you will need to be comfortable with risk; too much caution in the moment will equate to too little confidence, and this may result in you seeming unnatural, which is the antitheses of your role most often. There are of course times where you will be nervous; my advice is that, in such moments, use those nerves as part of your pretext. Let your nervous energy come out as you tell security that you are running late for a critical meeting.

This position on caution remains valid no matter the vector you are using—being too cautious on a vishing call where the target expects authenticity will likely lower your probability of success. Being cautious with a phish is a thing—it will show up in the length of the email you send. You will likely try to answer every question you can possibly come up with from the target's perspective in the body of your phish—a big no-no. Phishes are to be succinct and not say quite enough, piquing the target's curiosity or piquing some other mood or reaction so that they click on the phish's link. Too much caution on a network pen test will likely prevent you from seeing gaps and exploiting them. You need to be able to take calculated risks.

It's notable that there's a difference between being comfortable with risk and failing to analyze a situation, but OAMs has you strike a balance between the two. The balance can be found in seeking a solution as a problem comes into view. The slight caution that OAMs affords you is what aids the swift identification of a problem. Implementing the solution is a function of comfort with risk. Being comfortable with risk doesn't mean you avoid a problem or deny it exists altogether—it just means that you can be comfortable finding another avenue that isn't your first choice or that puts you at greater risk.

The way to reach something that resembles equilibrium between caution and risk-taking is to apply it with another component of AMs—visualizing outcomes. By further playing that game of mental chess, you should be able to think through the risk factors of the operation. Every move you make comes with a risk, and some risks are the unintended consequences of simply executing an attack. If you try to think about every single measure of risk involved, step-by-step, you will walk straight into failure. But keeping your end goal in mind and thinking through how your next move may impact how you achieve that goal is a good start. It will keep you balanced and on track. Keep a holistic assessment of the risk running in your mind.

To sum up, when executing the attack, you should not be overly or overtly cautious. There has to be a sense of comfort with risk when executing. There is, however, lots of room for caution preceding the execution, which, as you'll see, your DAMs will take care of. The biggest issue of discomfort with risk when executing an attack is that it can reveal you as an intruder. OAMs allows you to maintain a relaxed approach and to act without showing hesitation and avoid the dangers of overthinking.

The Art of Attack

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