Lenny's Product Pass (With new additions)

You’re midway through a pentesting engagement. Recon’s wrapped, and a couple of privilege escalation paths have already failed. You flip over to ChatGPT hoping for something useful, but it offers the usual: SUID binaries, kernel exploits, and weak folder permissions. It doesn’t know your host, the tools you've used, or what phase of the operation you're in—and that’s the real problem.

We started tinkering with a question: what would it take to make an assistant that thinks more like an operator under pressure? One that tracks what’s actually happening in your shell without having to copy and paste over and over again. It watches the flow of your session, reasons over what you’ve already done, and suggests next steps that are grounded in your actual operation, not pulled from some generic playbook.

This write-up shares what we’ve learned so far, what didn’t work, and where we think things could go. Would love feedback from folks building or breaking in the same space.

quantified•11h ago

For the newbie black hat, how useful is this to improve their chops in actual penetration?

sophia-martinez•9h ago

Good question — we’re thinking about it as a way to support operator training and tactical development.

It’s not about giving you the answer, but about exposing the range of reasonable next steps in a given situation. Because the system tracks prior commands and environment state, its suggestions can help newer operators learn how context influences decision-making — not just what can be done, but why certain moves make more sense at that moment.

In that sense, it’s more like a guided sparring partner than a shortcut! Still early days, but we’re curious how something like this could help folks build intuition under pressure. Got any thoughts?