Intro
Heyo folks. So on Twitter I asked a number of you what you wanted me to post about, and a number of you said that you'd like to hear what I've learned from working about a year in pentesting. Well, without further do I'm going to try and explain what I think are some of most important lessons I have learned from some of my recent and past jobs. There is a lot to cover so this post might be a little long but hopefully it will help some of you out there when encountering similar situations.
Lessons
Okay we are going to do this on a mixture of anonymised situation based scenarios which I have encountered as well as some general tips as I can't remember every situation :P
Always Relate To The Client
So this is one of the lessons that I had more trouble with but I had some specific scenario with a client that made me realise the importance of this. I was onsite with the client working a particularly disorganized job where things weren't working out and my technical contact was constantly pulling me off the job for various things such as updates on the testing and meetings with various people. This lead to tension between me and my technical contact as I was not particularly happy with being taken off the job to do these various elements and we were not seeing eye to eye with some of the arrangements that were being made to try get the pentest back on track.
Eventually though, I did find a solution that worked. What was it you ask? I looked at the situation from the perspective of the client. I realized that I needed to stop pushing the job from a pentester's perspective and start looking at how I could try help the company from the perspective of my technical point of contact. This is an important lesson and one I still use on my jobs today as it is important to realize that there is a time and place for being stern and pushing the fact that organizations need to get their shit together, organise themselves to be ready for a pentest, and make sure they fix their issues, but there is also a time to understand that there is a lot that goes on in order for an organization to be ready for a pentest and that there may be a lot of things going on behind the scene that you are not fully aware of that may explain why the organization can't patch that high risk issue you reported or get those credentials that you need to test the web API.
Therefore realize that everyone you work with is just another human trying to do their job. Once you realize that, you'll realize that even managers are just another person you need to relate to, albeit at a different level than an engineer which you might have to relate to on a more technical level. Get to understand the person, their problems, and think about how you can work to solve those problems, and you'll not only help to solve their problems, but you'll likely solve your problems in the process and will speed up your pentest in the process.
Realize That Not Everyone Has the Mindset for Pentesting
So this is more of something that I have noticed from watching people who have left pentesting as a whole, but I would like to point out that some people join pentesting but just don't have the right mindset for it. Now I may be wrong about this to some extent and I could look back on this and ask myself why the hell I wrote it but I have noticed some people who have joined pentesting recently who have no real self-seeking passion for knowledge and that intrinsic passion to learn more and experiment with things to figure out how to really solve the issue.
The problem with this is that your not always going to be able to ask people for help when your on site on a client site. You may have a website that requires some specific method to interact with it, and without being able to investigate, discover the internal details and craft a solution, your not going to be able to fix the issue. A somewhat better example though is that without having the drive to learn more, your not going to be able to push yourself to learn new technologies and exploitation methodologies that will allow you to provide the best possible solutions to your companies' clients. You are then facing the risk the company seek out more capable pentesters in the process, which leaves you with a situation of job instability if the company doesn't think you are doing as good a job as it expects from its pentesters.
This has lead to some people that I know leaving pentesting and going into software development instead; if I am being completely honest, I am really happy that they did. They were clearly more driven by the programming side of pentesting and did not always have the skills needed to deal with variety of customer situations that a pentester inevitably encounters. They did however know how to craft programs to solve a variety of problems, had good knowledge of programming and associated programs, and had the drive to create solutions to common problems they encountered, all things that are well suited for a programming job.
So, yeah that was a bit long winded, but essentially realize that you may end up working with people who are quite simply just not suited to pentesting. You're just going to have to deal with it and try and help them as much as you reasonably can, and hope that for their own sake they may find something that better suits their available skills and makes them happy, as you are not responsible for their decisions in life and ultimately they must make their own decisions regarding their job.
Your Going to Live in Hotels
One thing that I think people don't fully realize is just how much time you may end up spending away from home, family, etc as a consultant. Being a consultant isn't just a 9 to 5 (or in our case 5:30) job. It will require you to travel down to the client on the weekend, work after normal hours to understand that job that you have coming up, or edit the report for a previous client.
In fact this was actually one of things that I have seen several people complain about when they start working as a full time consultant. My response honestly? Get used to it. We have people in our office that I rarely if ever see. Why? Well some of them are just working from home as its too expensive to come into the office, but a fair number of them are onsite working for a client, and spend most of their month traveling between various client sites for associated onsite jobs. Its not uncommon to be fully booked for the month on onsite jobs with no associated "white days" (aka free days where you can catch up on work, do research, or whatever you like within reasonable limitations) for that month.
As a consultant you are expected to be able to travel to jobs as and when clients ask for you. That job could be up in Scottland, it could be way down South on the coast, it could be easily accessible by train, it could be a long car drive away, it all depends. You need to be ready to go anywhere, and adjust your travel and hotel plans to suit situations that may come up (prime example: train strikes, all the 3 star hotels being booked leaving you with only a local 2 star hotel to stay in (happened to me twice)).
So yeah, if your not ready to be flexible on a daily basis, pentesting may not be for you.
Be Prepared for Things to Go Wrong, and Realize Its Not Always Your Fault
I literally can't tell you about the number jobs where things have gone wrong. From missing credentials, to the client updating the site in the middle of testing, to missing authorization forms, to credentials being incorrect, to documentation not being supplied, there are many things that can go wrong in a pentest. Sometimes you may even feel that you caused all of this to happen and it can be overwhelming at times thinking that you might have forgotten something that you think caused all of this to happen.
The best way to deal with these sorts of situations I find is to expect that you may have to spend a day or a few hours on the first day dealing with issues and trying to get things sorted out, especially if its an onsite job (I find remote jobs typically tend to go quite smoothly minus potential access issues as there is less for the client to deal with in most cases). Be prepared to take an active part in trying to help the client out as it is likely that they may not fully understand what you need to conduct your test so you will have to explain it to them keeping in mind they may not be technical.
Also realize that most times when something goes horribly wrong its not entirely your fault. Sure, there may be some situations where you really did mess everything up, but 95% of the time, its either going to be both the client's and you or your company's fault. This may be because the job was not scoped correctly, because the client didn't supply appropriate details, because there was a lack of understanding of the technology, or any number other reasons. All you can do is try do your best to solve the situations you are responsible for and realize that you are not responsible for everything, and there are things that are beyond your control.
Ask Questions to Colleagues But Only If You Can't Find The Answer Yourself
Whenever you are pentesting, one of the most important things to realize is that your colleagues are around to help you. If you are seriously stuck or need advice about something, send them an email or walk up to them and ask them your question(s). Even managing pentesters still have questions about their job; everyone is still constantly learning and we all need to ask each other for help from time to time.
Do be careful though, as you can fall into a trap of asking questions too often instead of looking things up yourself, and you can end up just bothering fellow colleagues (something that I personally am trying to improve on). Therefore always make sure you have a concrete question you want to ask and that you have tried to look up the answer beforehand. This will prevent you asking questions that are a simple Google or internal website/wiki/documentation/etc lookup away from an answer.
Conclusion
Hopefully that helps some people who are starting out in pentesting. I may expand this more in the future, but this is what I was able to come up with in one night from my recollection of past events and jobs within the last year that stood out to me as being prominent in shaping my day to day activities pentesting or which taught me an important lesson.
Let me know if there are any lessons from your pentests you have learned - I would be interested to hear other people's experiences.
-tekwizz123
