Past, Present, and Future of AI agents

The intersection of AI and cybersecurity is changing faster than anyone expected, and that pace is creating both incredible innovation and brand-new risks we're only beginning to understand. From deepfake ads that fool even seasoned security professionals to autonomous agents capable of acting on our behalf, the threat landscape looks very different than it did even a year ago. To explore what this evolution means for everyday people and for enterprises trying to keep up, I'm joined by Chris Kirschke, Field CISO at Tuskira and a security leader with more than two decades of experience navigating complex cyber environments. Chris talks about his unconventional path into the industry, how much harder it is for new professionals to enter cybersecurity today, and the surprising story of how he recently fell for a fake Facebook ad that showcased just how convincing AI-powered scams have become. He breaks down the four major waves of InfoSec from the rise of the web, through mobile and cloud, to the sudden, uncontrollable arrival of generative AI. He then explains why this fourth wave caught companies completely off guard. GenAI wasn't something organizations adopted thoughtfully; it appeared overnight, with thousands of employees using it long before security teams understood its impact. That forced long-ignored issues like data classification, permissions cleanup, and internal hygiene to the forefront. We also dive into the world of agentic AI which is AI that doesn't just analyze but actually acts and the incredible opportunities and dangers that come with it. Chris shares how low-code orchestration, continuous penetration testing, context engineering, and security "mesh" architectures are reshaping modern InfoSec. Chris spends a lot of time talking about the human side of all this and why guardrails matter, how easy it is to over-automate, and the simple truth that AI still struggles with the soft skills security teams rely on every day. He also shares what companies should think about before diving into AI, starting with understanding their data, looping in legal and privacy teams early, and giving themselves room to experiment without turning everything over to an agent on day one. Show Notes: [00:00] Chris Kirschke, Field CISO at Tuskira, is here to explore how AI is reshaping cybersecurity and why modern threats look so different today. [03:05] Chris shares his unexpected path from bartending into IT in the late '90s, reflecting on how difficult it has become for newcomers to enter cybersecurity today. [06:18] A convincing Facebook scam slips past his defenses, illustrating how AI-enhanced fraud makes traditional red flags far harder to spot. [09:32] GenAI's sudden arrival in the workplace creates chaos as employees adopt tools faster than security teams can assess risk. [12:08] The conversation shifts to AI-driven penetration testing and how continuous, automated testing is replacing traditional annual reports. [15:23] Agentic AI enters the picture as Chris explains how low-code orchestration and autonomous agents are transforming security workflows. [18:24] He discusses when consumers can safely rely on AI agents and why human-in-the-loop oversight remains essential for anything involving transactions or access. [21:48] AI's dependence on context becomes clear as organizations move toward context lakes to support more intelligent, adaptive security models. [25:46] He highlights early experiments where AI agents automatically fix vulnerabilities in code, along with the dangers of developers becoming over-reliant on automation. [29:50] AI emerges as a support tool rather than a replacement, with Chris emphasizing that communication, trust, and human judgment remain central to the security profession. [33:35] A mock deposition experience reveals how AI might help individuals prepare for high-stress legal or compliance scenarios. [37:13] Chris outlines practical guardrails for adopting AI—starting with data understanding, legal partnerships, and clear architectural patterns. [40:21] Chatbot failures remind everyone that AI can invent policies or explanations when it lacks guidance, underscoring the need for strong oversight. [41:32] Closing thoughts include where to find more of Chris's work and continue learning about Tuskira's approach to AI security.  Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.  Links and Resources: Podcast Web Page Facebook Page whatismyipaddress.com Easy Prey on Instagram Easy Prey on Twitter Easy Prey on LinkedIn Easy Prey on YouTube Easy Prey on Pinterest Tuskira Chris Kirschke -LinkedIn