The Art of Attack. Maxie Reynolds

is also what keeps you in a sort of hunt mode as the attack unfolds, identifying any opportunities that present themselves and exploiting them with seeming ease and poise—all without letting the target know that you have any ulterior motive or missing a beat as you deviate from your original plan. It leads you to learn new things about your target and apply those lessons for the good of the objective. For example, you might not learn until you get on-site that they have upgraded their visitor system to a digital kiosk that can be circumvented with the standard out-of-the-box key code.

      There is also a sense of competitiveness with OAMs. It doesn't want to be beaten. Ever. It doesn't want to be merciful or helpful. It wants only to win. Your competitive drive is always influenced greatly by your determination to set and achieve goals. It should keep you striving for progress with a quiet but unrelenting focus. It's the peak of your curiosity and persistence combined. It is your competitive desire combined with critical thought that helps you match and surpass defenses meant to stop you. Your OAMs is powerful—a force to be reckoned with, neatly hidden behind a pretext or stealthy moves.

OAMs also guides the achievement of our objective through certain advantageous vectors. It does so by revealing facilitation in places you might not have considered looking otherwise, like vendors, suppliers, insurance providers, and building maintenance contractors. It helps you look at the world in an adversarial and alternative way. It sees through a lens that only identifies helpful or unhelpful data and information. OAMs wants to proceed and succeed. It's the machine that weaponizes information.

       Comfort and Risk

      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.

       Planning Pressure and Mental Agility

One of your greatest advantages as an EA is that you know you are attacking, whereas the target is typically oblivious. Often this advantage translates to the illusion of control—the tendency for all of us to overestimate our ability to dominate and manage events. Strictly speaking, you do not have control over the outcome of any operation; it's down to randomness or “luck.” You can do things, however, to steer the outcome in your favor. The initial reveal here is that an abundance of caution will hamper this ability to steer, whereas a relaxed, but risk-aware, approach will function and perform far more highly. This may seem difficult given that, as an attacker, you need to maintain extremely strong offensive mental agility.

      You should be focused, intense, aiming to win, and primed to take advantage of any opportunity for success that real-life attacks provide, also known as mental agility. Note that, even if you plan an attack within an inch of its life, you will still not be able to accurately account for the actions and reactions of your targets. Without mental agility, an attacker may be good, but they will never be great.

      Planning in and of itself will not lead you to feel pressure, but insisting you stick to the plan will. It is also likely lead you to failure. You must be able to interact and react to the environment. No one wakes up and says to themselves, “Well, today is the day I will not react to my environment.”

      Sometimes we get so set on winning that we get tunnel vision on the one route we want to take, not the one that's opening up in front of us. You must be able to adapt. When nothing is going as planned, you have to be able to pivot. When everything is going as planned, you should still recognize the opportunity to pivot, especially if it leads to a shortcut.

      I've had to pivot more times than I've had hot dinners, and thankfully, not all have led to success. One of my first jobs saw me turn up at a small office as an IT consultant, which wasn't all that far from the truth. I was promptly introduced to the facilities manager, who was exceptionally nice to me. She gave me a cup of tea, and I told her about my love of British biscuits because I saw some in the kitchen, and I am not above hinting. Mere minutes later I had enough to eat and to take home. News of an IT consultant's arrival soon traveled, and not too long after I had staff coming up to me inquiring about some issues they were having on their computers—enter the pivot!

I, of course, agreed to take a look so that I could open a command prompt—allows you to run programs, manipulate Windows settings, and access files by typing in commands, the perfect low-key privilege escalation I'd been looking for. After a few minutes poking around pretending I knew what I was doing, I opened Terminal and took a discreet photo and thought I'd be on my merry way—except someone asked me a very simple question that any IT professional would know, and I crumbled like a two-day-old British biscuit. They saw me crumble, and minutes later the whole operation was on its knees because the manager of the office insisted on calling my cover company, which didn't exist. All because I couldn't recall what RAM stands for. (I can now at all times.) I still managed to pivot. When there was no answer on the other end of the line, mainly because it was ringing the burner phone in my pocket, I soon began to act indignant. I left papers to sign and told them where they could send them and got on my way.

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