The Principles and Planning Stages of Pretexting

The Principles and Planning Stages of Pretexting

As with every skill, certain principles dictate the steps to performing that task. Pretexting is no different. The following is a list of principles of pretexting that you can use. By no means are these the only principles out there; maybe others can be added, but these principles embody the essence of pretexting:

1. The more research you do the better the chance of success
2. Involving your own personal interests will increase success
3. Using the Phone Should Not Reduce the Effort for the Social Engineer
4. The simpler the pretext the better the chance of success
5. The pretext should appear spontaneous
6. Provide a logical conclusion or follow through for the target

Provide a Logical Conclusion or Follow-through for the Target

Believe it or not people want to be told what to do. Imagine if you went to a doctor and he walked in, checked you over, wrote some things on his chart, and said, “Okay; see you in a month.” That would be unacceptable. Even in the event of bad news, people want to be told the next step and what to do.

As a social engineer, when you leave the target, you may need him to take or not take an action, or you may have gotten what you came for and just need to leave. Whatever the circumstance, giving the target a conclusion or follow-through fills in the expected gaps for the target.

Just as if a doctor checked you over and sent you home with no directions, if you engineer your way into a facility as a tech support guy and just walk out without saying anything to anyone after cloning the database, you leave everyone wondering what happened. Someone may even call the “tech support company” and ask whether he needed to do anything, or at worst you just leave the workers wondering. Either way, leaving everyone hanging is not the way to leave.

Even a simple, “I checked over the servers and repaired the file system; you should see a 22% increase in speed over the next couple days,” leaves the targets feeling as if they “got their money’s worth.”

The tricky part for a social engineer is getting the target to take an action after he or she is gone. If the action is vital for completion of the social engineer audit, then you may want to take that role upon yourself.

The requests you make should match the pretext, too. If your pretext is being a tech support guy, you won’t “order” people around with what they must and must not do; you work for them. If you are a UPS delivery person, you don’t demand access to the server room.

As mentioned earlier, more steps may exist for perfecting a pretext, but the ones listed in this chapter can give a social engineer a solid foundation to build a perfectly believable pretext.

You might be asking, “Okay, so you listed all these principles, but now what?” How can a social engineer build a well-researched, believable, spontaneous-sounding, simple pretext that can work either on the phone or in person and get the desired results? 

The Pretext Should Appear Spontaneous

Making the pretext appear spontaneous goes back to my point on using an outline versus using script.

Outlines will always allow the social engineer more freedom and a script will make the social engineer sound too robotic. It also ties in to using items or stories that interest the social engineer personally.

If every time someone asks you a question or makes a statement that requires you to think, and you go, “Ummmm” and start to think deeply, and you cannot come back with an intelligent answer, it will ruin your credibility.

Of course many people think before they speak, so this is not about having the answer in one second, but about having an answer or a reason for not having the answer. For example, in one phone call I was asked for a piece of information I didn’t have. I simply said, “Let me get that.” I then leaned over and made it sound like I was yelling for a workmate: “Jill, can you please ask Bill to give me the order form for the XYZ account? Thanks.”

Then as “Jill” was getting the paper for me I was able to obtain the data I needed and the paper was never brought up again. I have compiled a small list of ways that you can work on being more spontaneous:

Don’t think about how you feel. This point is a good one, because often in a pretext if you overthink you will start to add emotion into the mix, which can cause fear, nervousness, or anxiety, all of which lead to failure. On the other hand, you might not experience nervousness

or fear, but over-excitement, which can also cause you to make a lot of mistakes.

Don’t take yourself too seriously. Of course, this is great advice in life, but it applies wonderfully to social engineering. As a security professional you have a serious job; this is a serious matter. But if you’re not able to laugh at your mistakes, you may clam up or get too nervous to handle a small bump in the road. I am not suggesting you take security as a joke. In your mind, though, if you view a potential failure as the pinnacle of failure in your life, the pressure you create can cause just what you fear the most. Minor failures can often lead to greater success if you have the ability to roll with it.

Learn to identify what is relevant. I like to phrase this concept as, “Get out of your head and into the world,” which is more great advice. A social engineer may be trying to plan three steps ahead and in the meantime miss a vital detail that can cause the pretext to fall apart.

Be quick to identify the relevant material and information around you, whether it is the target’s body language, words spoken, or microexpressions, and assimilate the information into the attack vector.

Also keep in mind that people can tell when someone isn’t really listening to what they are saying. Getting the feeling that even unimportant sentences are falling on deaf ears can be a massive turnoff for many people. Everyone has experienced being with someone who just didn’t seem to care what he or she is saying. Maybe that person even had a legitimate reason to be thinking on a different path, but doing it is still a turnoff.

Be sure to listen to what your target is saying. Pay close attention and you will pick up the details that are very important to them and in the meantime, you might hear something to help you in your success.

Seek to gain experience. This concept goes back to what you will probably see repeated four million times in this tutorial—practice. Gaining experience through practice can make or break the pretext.

Practice spontaneity with family and friends and total strangers with absolutely no goal in mind but to be spontaneous. Strike up conversations with people, but not in a scary stalker kind of way— simple little conversations can go a long way toward making you feel comfortable being spontaneous.

These points can definitely give a social engineer the upper hand when it comes to pretexting. Having the ability to appear spontaneous is a gift. 

The Simpler the Pretext, the Better the Chance of Success

“The simpler, the better” principle just can’t be overstated. If the pretext has so many intricate details that forgetting one will cause a social engineering failure, it is probably going to fail. Keeping the story lines, facts, and details simple can help build credibility.

Dr. Paul Ekman, a renowned psychologist and researcher in the field of human deception, cowrote an article in 1993 entitled, “Lies That Fail.” In that article he says

[t]here is not always time to prepare the line to be taken, to rehearse and memorize it. Even when there has been ample advance notice, and a false line has been carefully devised, the liar may not be clever enough to anticipate all the questions that may be asked, and to have thought through what his answers must be. Even cleverness may not be enough, for unseen changes in circumstances can betray an otherwise effective line. And, even when a liar is not forced by circumstances to change lines, some liars have trouble recalling the line they have previously committed themselves to, so that new questions cannot be consistently answered quickly.

This very salient point explains clearly why simple is better. Trying to remember a pretext can be almost impossible if it is so complex that your cover can be blown by a simple mistake. The pretext should be natural and smooth. It should be easy to remember, and if it feels natural to you, then recalling facts or lines used previously in the pretext will not be a task.

To illustrate how important it is to remember the small details I want to share a story with you. Once upon a time I tried my hand at sales. I was placed with a sales manager to learn the ropes. I can recall my first call with him. We drove up to the house, and before we left the car he looked at the info card and told me, “Remember, Becky Smith sent in a request card for supplemental insurance. We will present the XYZ policy. Watch and learn.” In the first three minutes of the sales call he called her Beth and Betty.

Each time he used the wrong name I saw her demeanor change and then she would say quietly, “Becky.” I feel we could have been giving away gold bullion and she would have said no. She was so turned off that he couldn’t get her name right that she was not interested in listening to anything. This scenario really drives home the point of keeping the simple facts straight.

In addition to remembering the facts, it is equally important to keep the details small. A simple pretext allows for the story to grow and the target to use their imagination to fill the gaps. Do not try to make the pretext elaborate, and above all, remember the tiny details that will make the difference in how people view the pretext.

On the other hand, here is an interesting tidbit: A popular tactic used by famous criminals and con men is to purposely make a few mistakes. The thought is that “no one is perfect,” and a few mistakes make people feel at home. Be cautious with what types of mistakes you decide to make if you employ this tactic because it does add complexity to your pretext, but it does make the conversation seem more natural. Use this tip sparingly, however you decide to proceed, keep it simple.

Let me tie all this together with a few examples that I have used or seen used in audits. After some excellent elicitation on the phone, a nameless social engineer had been given the name of the waste removal company. A few simple Internet searches and he had a usable and printable logo. There are dozens of local and online shops that will print shirts or hats with a logo on it.

A few minutes of aligning things on a template and he ordered a shirt and ball cap with the logo of the waste company on it. A couple days later, wearing the logo-laden clothing and carrying a clipboard, the social engineer approached the security booth of the target company.

He said, “Hi, I’m Joe with ABC Waste. We got a call from your purchasing department asking to send someone over to check out a damaged dumpster in the back. The pickup is tomorrow and if the dumpster isn’t repairable I will have them bring out a new one. But I need to run back there and inspect it.”

Without blinking, the security officer said, “OK, you will need this badge to get onsite. Just pull through here and drive around the back and you will see the dumpsters there.” The social engineer had a free pass to perform a very long and detailed dumpster dive but wanted to maximize his potential so went in for the kill with this line. While looking at his clipboard he said, “The note says it is not the food dumpsters but one of the ones where paper or tech trash goes. Which block are those in?”

“Oh, just drive the same way I told you and they are in the third bay,” replied the security guard. “Thanks,” said Joe.

A simple pretext, backed up by clothing and “tools” (like the clipboard), and the storylines were simple to remember and not complex. The simplicity and lack of detail actually made this pretext more believable, and it worked. Another very widely used pretext is that of the tech support guy. This one only requires a polo shirt, pair of khakis, and small computer tool bag. Many social engineers employ this tactic to get in the front door because the “tech guy” is usually given access to everything without supervision. The same rules apply: keeping the storyline simple will help make this particular pretext very real and believable.

Using the Phone Should Not Reduce the Effort for the Social Engineer

In recent years, the Internet has come to dominate certain more “impersonal” aspects of social engineering, whereas in days past the phone was an integral part of social engineering. Because of this shift, many social engineers do not put the energy or effort into phone usage that can make it truly successful.

This topic is here to show that the phone is still one of the most powerful tools of the social engineer and the effort put into using it should not be diminished due to the impersonal nature of the Internet.

Sometimes when a social engineer plans a phone attack his thinking may differ because using the Internet might appear easier. Note that you should plan to put the same level of effort, the same level and depth of research and information gathering, and most importantly the same level of practice into your phone-based social engineering attacks. I was once with a small group that was going to practice phone presentations. We outlined the proper methods, the tone, the speed, the pitches, and the words to use. We outlined a script (more on this in a minute) and then launched a session.

The first person made the call, got on the phone with someone, and messed up the first few lines. Out of complete embarrassment and fear he just hung up on the person. There is a very good lesson there—the person on the other end of the phone has no clue what you are going to say, so you can’t really “mess up.” Practice sessions can help you learn how to handle the “unknowns” caused by your accidentally altering something in your script that throws you off base.

If you are not as fortunate to have a group to practice or hone these skills with, you will have to get creative. Try calling family or friends to see how far you can get manipulating them. Another way to practice is to record yourself as if you were on the phone and then play it back later to hear how you sound.

I personally feel that using an outlined script is very important. Here is an illustration: suppose you had to call your phone company or another utility. Maybe they messed up a bill or you had another service problem and you are going to complain. After you explain yourself to the rep, telling her how upset and disappointed you are, and the rep does absolutely nothing for you, she says something like, “XY&Z is committed to excellent service; have I answered all your questions today?” If the drone behind the phone thought for one second about what she was asking she would realize how silly it is, right? This is what happens when you use a written-out script instead of an outline. An outline allows you “creative artistic freedom” to move around in the conversation and not be so worried about what must come next. Using the phone to solidify your pretext is one of the quickest methods inside your target’s door. The phone allows the social engineer to “spoof,” or fake, almost anything. Take into consideration this example: If I wanted to call you and pretend I was in a bustling office to add to the pretext I was trying to use, I could simply grab the audio track from Thriving Office (www.thrivingoffice.com/). This site offers a track called “Busy” and another called “Very Busy.” From the creators: “This valuable CD, which is filled with the sounds people expect to hear from an established company, provides instant credibility. It’s simple, effective, and guaranteed!”

That sentence alone is filled with social engineering goodness—filled with what people expect to hear from an established company. Already you can see that the CD is geared to fill expectations and provide credibility (at least, in the target’s mind, after his expectations are met), thereby automatically building trust.

In addition, spoofing caller ID information is relatively simple. Services like SpoofCard (www.spoofcard.com) or using homegrown solutions, allows a social engineer to tell the target you are calling from a corporate headquarters, the White House, or the local bank. With these services you can spoof the number to be coming from anywhere in the world.

The phone is a deadly tool for social engineers; developing the habits to practice using it and to treat it with utter respect will enhance any social engineer’s toolset for pretexting. Because the phone is such a deadly tool and has not lost its effectiveness, you should give it the time and effort it deserves in any social engineering gig.

Involve Personal Interests to Increase Success

Using your own personal interests to increase the chances of a successful social engineering move seems very simple but it can go a long way in convincing the target that you are credible. Nothing can ruin rapport and trust faster than a person who claims to be knowledgeable about a topic and then falls short. As a social engineer, if you have never seen a server room before and have never taken a computer apart, trying to play the part of a technician can be a quick path to failure. Including topics and activities in your pretext that you are interested in gives you a lot to talk about and gives you the ability to portray intelligence as well as confidence.

Confidence can go a long way toward convincing the target you are who you say you are. Certain pretexts require more knowledge than others (for instance, stamp collector versus nuclear researcher) to be convincing, so again research becomes the recurring theme. Sometimes the pretext is simple enough that you can get the knowledge by reading a few websites or a book.

However you gain the knowledge, researching topics that personally interest you, as the social engineer, is important. After you pick up on a story, aspect, service, or interest that you have a lot of knowledge in or at least feel comfortable discussing, see whether that angle can work.

Dr. Tom G. Stevens, PhD, says, “It is important to remember that self confidence is always relative to the task and situation. We have different levels of confidence in different situations.” This statement is very important, because confidence directly links to how others view you as a social engineer. Confidence (as long as it is not overconfidence) builds trust and rapport and makes people feel at ease. Finding a path to your target that offers you the chance to talk about topics you are comfortable with, and that you can speak about with confidence, is very important.

The More Research You Do, the Better the Chance of Success

This principle is self-explanatory, but it can’t be said enough—the level of success is directly connected to the level and depth of research. As discussed in earlier tutorial on Information Gathering, it is the crux of successful social engineering. 

The more information a social engineer holds the more chances he or she has of developing a pretext that works. 

Remember the story I told in Tutorial - Information Gathering about Attacker (Social Engineer) and how he convinced a high-level executive to visit his “stamp collection” site online? At first glance, the path inside that company might have seemed to be something to do with financial, banking, fund raising, or something along those lines because it was a banking facility. The more research Attacker (Social Engineer)  did, the clearer it became that the pretext could be a person who was selling a stamp collection. Finding out what the executive’s interests were allowed Attacker (Social Engineer)  to find an easy way into the company, and it worked.

Sometimes those little details that are what make the difference. Remember, no information is irrelevant. While gathering information, looking for stories, items, or aspects of a personal nature is also a good idea. Using a target’s personal or emotional attachments can enable you to get a foot in the door. If the social engineer finds out that every year the CFO donates a sizable sum to a children’s cancer research center, then a pretext that involves fund raising for this cause could very likely work, as heartless as it sounds.

The problem is that malicious social engineers use pretexts that feed on emotions without a second thought. After the attacks on the Twin Towers in New York City on September 11, 2001, many malicious hackers and social engineers used the losses of these people to raise funds for themselves via websites and emails that targeted people’s computers and fake fund raisers that obtained funds from those with a giving heart. After the earthquakes in Chile and Haiti in 2010, the same things occurred where many malicious social engineers developed websites that were positioned as giving out information on the seismic activity or the people who were lost. These sites were encoded with malicious code and hacked people’s computers.

This is even more evident directly after the death of a movie or music star. Search engine optimization (SEO) and marketing geniuses will have the search engines pulling up their stories in a matter of hours. Along with marketers, malicious social engineers will take advantage of the increased search engine attention by launching malicious sites that feed off that SEO. Drawing people to these sites, they harvest information or infect them with viruses.

As a social engineering auditor, I can use an employee’s emotions to show a company that even people with seemingly good intentions can trick a company’s employees into giving access to valuable and business-ruining data.

All these examples solidify the point that the better a social engineer’s information-gathering and research-gathering process, the better chance he has at finding some detail that will increase the chances of a successful pretext.