8669804656?profile=original

Formal Modeling and Automation is one of the things I love. I try to model everything and sometimes modeling helps and sometime it lands me in trouble. It helped me when I tried to model Penetration Testing and worked with my co-founder to design our first version of automated Penetration Testing Tool at iViZ. Where it did not help is in dancing. I think I am a poor dancer since my mind thinks modeling. By the time I model the step in my mind, I miss the beat. I believe there are a few things which we need to do from heart and not from mind.

I was thinking why in the context of today’s maturity of Artificial Intelligence (AI) we cannot fully automate Penetration Testing (or “maybe” we will never be able to). Here are the top reasons that come to my mind.

( Read More: Major Components Of IT GRC Solutions )

Penetration Testing: Multi Stage Attack Planning is a PSPACE Complete Problem

In Penetration Testing, attack chaining becomes a critical element in terms of strategizing as well as executing some brilliant hacks. Human mind sometimes can compute some brilliant attack plans in just a jiffy. However, when we try to model this as a standard “AI Planning” problem, we get into a mess. Every exploit/attack can be modeled as an action with precondition and post condition. So, the standard solution we can think of is to use “Planning Algorithms” to build the entire attack graph. However, the challenge is with state explosion and we will immediately run out of memory (PSPACE Complete Problem). Though approximations can help, it can never find all the possible attack paths the moment the number of nodes increases beyond a threshold. However, when it comes to coverage, AI would definitely do better than humans (since humans get bored).

Modeling Creativity is a Hard Problem

There had been some work in terms of Artificial Creativity. We do have AI programs writing Poems (Flowerewolf). However we are quite far from creating automation that can match the human creativity. There are potential ways to model creativity. As an example you can model the knowledge from one field and apply it in a completely different field and in some cases you may end up with a "creative model". However not much of work has happened to model human creativity in the field of ethical hacking.

( Read More: Incident Response: How To Respond To A Security Breach During First 24 Hours (Checklist) )

Programs cannot Question the Assumptions

Human minds can question the fundamental assumptions. However a program runs on fundamental assumptions. Einstein challenged the assumptions of Newton. Heisenberg challenged the assumptions of Einstein and the game goes on. Any good pen tester/hacker challenges the assumption. When we broke Microsoft Bit locker encryption we challenged the assumption of the coders that from user land BIOS memory cannot be accessed. A program does not have the capability to challenge the assumptions and that is a severe limitation when it comes to automating Penetration Testing.

“Artificial Intuition” is still in early days

Humans have intuition. As per wiki- “Intuition is the ability to acquire knowledge without inference and/or the use of reason. Intuition provides us with beliefs that we cannot justify in every case”. We can sometime solve some brilliant problem without the use of any reasoning. Artificial Intuition is there to model this but we are still in quite a primitive state to match what our brains can do.

I am a big believer of AI and a bigger believer of the human mind. We did use some decent bit of AI to automate Penetration Testing during our iViZ days. While doing that I learn’t more of what we cannot do than what we can do. I am sure with time AI will get better but will we ever be able to do Penetration Testing without the humans?

 

More:  Join the community of 3000+ Chief Information Security Officers.  Click here

★
★
★
★
★
Votes: 0
E-mail me when people leave their comments –

You need to be a member of CISO Platform to add comments!

Join CISO Platform

Join The Community Discussion

CISO Platform

A global community of 6K+ Senior IT Security executives and 40K+ subscribers with the vision of meaningful collaboration, knowledge, and intelligence sharing to fight the growing cyber security threats.

Join CISO Community Share Your Knowledge (Post A Blog)
 

 

 

Turbo Talks: 20 Years of AppSec — What AI Changes, and What It Doesn't

  • Description:

    Turbo Talks is a free 20-minute live session series on agentic AI pentesting and AI safety for security leaders, hosted by CISO Platform. Technology partner: FireCompass.

    Speaker: Ed Adams, Distinguished Research Fellow, Ponemon Institute · Advisor, FireCompass

    Ed is a Distinguished Research Fellow at the Ponemon Institute, founded the Application Security Industry Consortium (later SAFECode), and led Security Innovation as CEO for 20+ years.…

  • Created by: Priyanka Aash
  • Tags: turbo talks, appsec, ai

Turbo Talks: Safe AI Agents — Guardrails, Scope Enforcement and Governance

  • Description:

    Turbo Talks is a free 20-minute live session series on agentic AI pentesting and AI safety for security leaders, hosted by CISO Platform. Technology partner: FireCompass.

    Speaker: Bikash Barai, Founder & CEO, FireCompass

    As offensive AI agents get more capable, control becomes the harder problem. Practical guardrails and governance for deploying them safely.

    Time: 11:30 AM ET / 7:30 PM GST / 9:00 PM IST ·…

  • Created by: Priyanka Aash
  • Tags: turbo talks, agentic ai, ai safety

CISOPlatform Breakfast Mumbai: Offensive Security for CISOs

  • Description:

    Theme: Offensive Security for CISOs — Validating Exposure at Attacker Speed

    A closed-door breakfast for CISOs and heads of security. Peer discussion under the Chatham House rule, not a product presentation.

    What the table will work through

    1. Exploit windows in days, not months. Edge devices, CI/CD and AI gateways were all exploited within weeks of disclosure this autumn (GitLab CVE-2026-97229, Cisco ASA/FTD…
  • Created by: Priyanka Aash
  • Tags: ciso breakfast, mumbai, offensive security, pentesting

CISOPlatform Dinner Delhi: Red Team Stories and 2027 Priorities

  • Description:

    Theme: Red Team Stories and Offensive Security Priorities for 2027

    An invite-only dinner for CISOs and security leaders in Delhi. Informal peer conversation under the Chatham House rule.

    Conversation starters

    • What did attackers (or your red team) find first in your environment, and what did you change after?
    • AI agents on both sides: attackers automating exploitation, and defenders using agents to pentest.
    • Your top…
  • Created by: Priyanka Aash
  • Tags: ciso dinner, delhi, offensive security, red teaming