Join me at the Chicago Cloud Computing Meetup on Thursday, September 4, 2025 for an engaging session with security researcher and speaker Jayson E. Street, where we’ll explore modern social engineering and the role AI plays in transforming phishing and vishing attacks.

Event Highlights

• Real-world demonstrations of social engineering across physical and cloud environments
• How AI amplifies phishing and vishing and what defenders need to know
• Practical steps to shift from “security awareness” to “situational awareness”
• Network with fellow cloud and security professionals

Icarus’s Flight and Other Dangers of Being Among the Clouds

Jayson will start this session by showing real world examples of how he robs banks & other places (like cloud data centers) via remote recon, walking in & phishing. We will then learn how he evolved to vishing with the help of AI. Because like it or not AI is transforming social engineering. Using tools like ChatGPT, Gemini, and Copilot, attackers can make phishing and vishing attacks nearly impossible to distinguish from legitimate Interactions. His presentation will demonstrate how virtually anyone with a pulse can now use AI to craft sophisticated phishing sites and conduct vishing operations with unprecedented subtlety and effectiveness. These next-generation techniques are transforming the landscape of social engineering.

We will learn how to leverage these techniques to transform an organization’s, traditional, “security awareness” mentality into a “situational awareness” mindset. Using real-world examples, he’ll demonstrate turning potential threats into teachable moments.

Speaker: Jayson E. Street

A “notorious hacker” by FOX25 Boston, “World Class Hacker” by National Geographic Breakthrough Series, a “paunchy hacker” by Rolling Stone Magazine and, as a “Change Agent” by the Director of Counter Intelligence at the Pentagon! He however prefers if people just refer to him simply as a Hacker, Helper & Human.

He’s a Simulated Adversary for hire. The author of the “Dissecting the hack: Series” (which is currently required reading at 7 colleges in 4 countries that he knows of). Also the DEF CON Groups Global Ambassador.

He’s spoken at conferences & summits in over 50 countries such as DEF CON, Le Hack, GISEC, IT-Defense, SYSCAN and at several other ‘CONs & colleges on a variety of Cyber Security/Hacking subjects. He also was asked to speak at the Pentagon on his revolutionary process of Situational Awareness training.

He loves to explore the world & networks as much as he can. He has successfully robbed banks, hotels, government facilities, Biochemical companies, etc.. on five continents (Only successfully robbing the wrong bank in Lebanon once all others he was supposed to)!

He is a highly carbonated speaker who has partaken of Pizza from Bulgaria to Brazil & China to The Canary Islands. He does not expect anybody to still be reading this far but if they are please note he was proud to be chosen as one of Time’s persons of the year for 2006.

Event Details

Date: Thursday, September 4, 2025
Time: 6:00 PM - 8:00 PM
Location: Microsoft Chicago Office, 200 E Randolph St, Suite 200, Chicago, IL 60601

Registration required: When you register, please include your first and last name. The Aon Center security team will need this information to allow you access to the building.

Register here: Chicago Cloud Computing Meetup - September 2025 Event