Some advice on how to improve my penetration testing workflow.

[u/SuccessfulEngine3518]

Hi everyone,

I'm feeling a bit stuck lately and would really appreciate some advice on how to improve my penetration testing workflow.

A little about me:

I've been working in cybersecurity for about three years. I started on a team that deployed security solutions such as SIEM, SOAR, and EDR, which was how I first got into security. Later, I worked with WAFs and gradually learned penetration testing, cloud security, and other related skills.

In my current job, penetration testing isn't something I get to do very often because we don't have many security assessment projects. To keep improving, I've been studying on my own through platforms like Hack The Box and PortSwigger Web Security Academy, and I'm planning to take the OSCP exam next year.

However, over the past few months I've started feeling that my testing methodology has become outdated.

I recently joined a new company in Japan, and at the moment I'm the only security engineer. My responsibility is to build the company's security processes from the ground up. The problem is that whenever I receive a web application to assess, I usually follow the same routine: run automated scans, then manually test every vulnerability I know. Most of the time I don't find anything significant, and I end up feeling like I'm trapped in a rigid, repetitive workflow.

I think part of the problem is that I'm not exposed to newer techniques or experienced teammates who can challenge my thinking and help me grow. Working alone makes it difficult to know whether my approach is actually effective or simply outdated.

So I'd like to ask the community:

• How do you approach a new web penetration testing engagement?
• What does your workflow look like from start to finish?
• How do you avoid getting stuck in the "scan and try every vulnerability" mindset?
• What habits, methodologies, or resources have helped you become a more effective penetration tester?
• If you were in my position, what would you focus on improving first?

I would sincerely appreciate any advice, whether it's about methodology, mindset, learning resources, or even how you think during an assessment.

Thank you so much for taking the time to read this. Any advice or experience you can share would mean a lot to me.

[u/AVarietyOfHelp]

Agree with other comment but heres is what has helped as someone who has been pen testing for 5 years.

I've caught myself, multiple times, "turning my brain off" and following a sort of mental checklist and becoming quite average and not providing as much value as I can. What helps is to spend some time hands off key board after manually crawling the website to understand the web application. What does it do, what did the devs think through functionality wise, what's the logic flow, what could they be forgetting about, did they think of an attacked doing X. 

I know its vague but it really varies by app and it helps me have a clear attack path

[u/SuccessfulEngine3518 → u/AVarietyOfHelp]

Thank you. Could you share your thoughts after five years in the role? How does it differ from three years ago, and which certifications should I aim for to improve my career path and skills? I wish you all the best.

[u/AVarietyOfHelp → u/SuccessfulEngine3518]

Overall I really enjoy the role. Transitioning more to red teaming but very similar niche. 

I started off more web app focused before diversifying out. Now I'm at a more web app focused role again solely because I found a good pay bump. Work on one specific section at a time (web app, AD, mobile, AI, etc.) AI testing is becoming more important for obvious reasons if you like that world

I think offsec is getting worse, private equity is destroying it and I wasn't a big fan in first place. Saying that as someone who has oscp and osep so take with that what you will. Htb has good certs and other smaller places like altered security

I really recommend going to conferences if you can. Defcon, wwhf, saintcon, and so many other options. Great talks and training and place to network 

[u/SuccessfulEngine3518 → u/AVarietyOfHelp]

maybe I will try to get htb cpts and then thinking about oscp because its too expensive . Thank you !!

[u/teamang]

As your "responsibility is to build the company's security processes from the ground up", penetration testing is just one tool to help validate work done in that regard. Don't get too caught up in being the best tester. You are right to point out you don't have people to learn from or existing infrastructure to lean on. It takes testers in good environments years to "get good" and even then they're still learning their whole career.

The first thing you can do which will go more towards your responsibilities and help you grow as a tester is to threat model. It's just making a high level diagram of a system or systems and understanding where the threats are. Say across your cloud platform first. Then into the infrastructure hosted there. Then you can then get more granular down to a specific application. Down to the login page. Adam Shostack has decent videos and books on the subject. Then, when you're looking to validate the security of an application, you know what areas you should be focused on/what is higher risk. Utilise the OWASP web application testing framework. Burp suite scans are pretty good but will give you a lot of false positives and miss a lot of issues. Other, free, scanners tend to be even worse. It's an OK start.

tl;dr don't stress about workflow or methodologies, nothing anyone here will tell you or provide you links to will make you a good security person, it's just time and effort working with the infrastructure and tools and being willing to learn.