Chatting with Rachael (ChatGPT) about Pentesting

by prof. Volker Skwarek, [email protected]

In this interview, ChatGPT is challenged with the general subject of penetration testing. I wanted to know more about ChatGPT’s knowledge about pentesting and how far it would guide me with precise procedures for testing. Last but not least, I also wanted to know a little more about ChatGPT.

The answers were surprisingly good, even if they were not finally satisfying.

This text provides a cut version of the full interview as indicated by the ellipses […] . This can be downloaded from the author’s podcast cast-notes site as provided at the end of this article.

While preparing for my interview with ChatGPT I was a bit nervous: Will it provide sufficient answers? How deep can I ask for technical details? Will it understand me and my questions? 

For better and more personal communication, I decided to ask ChatGPT if it minds being called Rachael – in memory of the android in the movie "Blade Runner". ChatGPT agreed. Therefore, I gave her the long name RachaelChatGPT, to be read as Rachael – powered by ChatGPT.

I wanted to digress only a little in the interview; I was following a strict guideline. However, I still had my thoughts and mind during the interview, which are printed in upright non-bold letters. 

[…]

Volker: Okay. Thank you. Let's now get....