I've presented this paper at Bsides Delhi 2017, cyber security conference This is the age of Automation, Artificial Intelligence and Machine learning. Even the most sophisticated tasks are being automated. Then why can’t we do the same for security testing as well? Pen-testing as a profession, we will have to repeat a lot of boring tasks on a daily basis. I have tried a lot of ways to automate some tasks using various methods. Finally ended up with Hubot from GitHub, which is an automation/AI Chat framework developed by GitHub using node.js Hubot is popular in the technology world; mostly used for DevOps, ChatOps, DFIR etc This presentation is all about customizing this bot and making it a virtual assistant only for web application testing; we can treat this bot as a person with huge amount of knowledge about information security; it can do so many things it was trained to do via a natural human language interface. Refer the slides for more detailed information!