Past, Present, and Future of AI agents
Easy Prey
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...
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You Are Traceable with OSINT
Easy Prey
Publicly available data can paint a much clearer picture of our lives than most of us realize, and this episode takes a deeper look at how those tiny digital breadcrumbs like photos, records, searches, even the background of a Zoom call can be pieced together to reveal far more than we ever intended. To help break this down, I’m joined by Cynthia Hetherington, Founder and CEO of The Hetherington Group, a longtime leader in open-source intelligence. She also founded Osmosis, the global association and conference for OSINT professionals, and she oversees OSINT Academy, where her team trains...
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Anyone Could Walk In
Easy Prey
Sometimes we forget how much trust we place in the little things around us like a lock on a door or a badge on someone’s shirt. We see those symbols and assume everything behind them is safe, but it doesn’t always work that way. A person with enough confidence, or the right story, can slip through places we think are locked down tight, and most of us never notice it’s happening. My guest today is Deviant Ollam, and he’s one of the rare people who gets invited to break into buildings on purpose. He talks about how he fell into this unusual line of work, the odd moments that shaped his...
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The Scam You Never See Coming
Easy Prey
Fraud today doesn’t feel anything like it used to. It’s not just about somebody skimming a credit card at a gas pump or stealing a check out of the mail. It has gotten personal, messy, emotional. Scammers are building relationships, earning trust, and studying the little details of our lives so they can strike when we’re tired, distracted, or dealing with something big. And honestly, most people have no idea how far it’s gone. My guest, Ian Mitchell, has spent more than 25 years fighting fraud around the world and leading teams in the financial sector. He’s the founder of The Knoble,...
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Hacking AI
Easy Prey
AI has brought incredible new capabilities into everyday technology, but it’s also creating security challenges that most people haven’t fully wrapped their heads around yet. As these systems become more capable and more deeply connected to the tools and data we rely on, the risks become harder to predict and much more complicated to manage. My guest today is Rich Smith, who leads offensive research at MindGard and has spent more than twenty years working on the front lines of cybersecurity. Rich has held leadership roles at organizations like Crash Override, Gemini, Duo Security, Cisco,...
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The Ransomware War
Easy Prey
Ransomware isn’t a lone hacker in a hoodie. It’s an entire criminal industry complete with developers, brokers, and money launderers working together like a dark tech startup. And while these groups constantly evolve, so do the tools and partnerships aimed at stopping them before they strike. My guest today is Cynthia Kaiser, former Deputy Assistant Director of the FBI’s Cyber Division and now the Head of the Ransomware Research Center at Halcyon. After two decades investigating global cyber threats and briefing top government leaders, she’s now focused on prevention and building...
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Opportunistic Crimes
Easy Prey
Criminals are always adapting. Whether it’s copper wiring stripped from job sites or porch pirates grabbing deliveries in broad daylight, they keep finding new ways to take what isn’t theirs. But maybe prevention isn’t about harsher punishment or more cameras. Maybe it’s about smarter design and understanding what drives people to steal in the first place. My guest today is Dr. Ben Stickle, a professor of criminal justice at Middle Tennessee State University and one of the country’s top researchers on property crime. Before entering academia, he worked in law enforcement, which gives...
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Post Scam Guidebook
Easy Prey
Fraud usually gets talked about in numbers like how much money was stolen, how many people were affected, how many cases got filed. But behind every one of those numbers is a person who’s been blindsided, manipulated, or left trying to rebuild trust in others and in themselves. This episode shifts the focus back to those human stories and the fight to protect them. My guest, Freddie Massimi, has spent more than a decade helping scam victims find both financial and emotional recovery, bringing empathy and understanding to a field that too often feels cold and procedural. As a certified...
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Can You Trust Anything Online
Easy Prey
You think you’d never fall for a scam until you meet someone like Kitboga. He’s a software engineer who’s turned his curiosity about online fraud into a full-time mission to outsmart scammers and protect the people they target. His YouTube channel, The Kitboga Show, has millions of followers and nearly a billion views, thanks to his mix of humor, empathy, and clever ways of exposing how scams really work. In our conversation, Kit opens up about how this all started, what it’s really like to spend hours pretending to be a scam victim, and how organized crime has turned fraud into a...
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Real Time Fraud Detection
Easy Prey
Everywhere you turn, someone’s trying to fake something like an image, a voice, or even an entire identity. With AI tools now in almost anyone’s hands, it takes minutes, not days, to create a convincing fake. That’s changed the game for both sides. The fraudsters have new weapons, and the rest of us are scrambling to keep up. The real question now isn’t just how to stop scams, but how to know who or what to trust online. My guest today, Bala Kumar, spends his days on the front lines of that battle. He’s the Chief Product and Technology Officer at Jumio, a company working to make...
info_outlineCybercrime continues to evolve in sophistication and scale, with attackers running their operations much like businesses. From ransomware gangs with customer support desks to AI-generated phishing campaigns that erase traditional red flags, scams are becoming harder to detect and stop.
In this episode, David Bittner, host of the CyberWire Daily Podcast, shares his perspective on the changing landscape of fraud and cyberattacks. Drawing on his background in media, theater, and podcasting, as well as years of reporting on security issues, he explains how both criminals and defenders are using AI, why ransomware has exploded instead of fading, and how scams exploit human trust and expectations..
David also talks about common scams hitting people today, from toll violation texts and fake bank calls to romance scams on social media. He recounts personal experiences of being targeted, including a Facebook credential-harvesting attempt and an exit-ramp “out of gas” con, to show that no one is immune. Looking ahead, he predicts existing scams will keep evolving, AI will continue to raise the stakes, and defenders may eventually need AI “agents” watching out for them in real time.
Show Notes:
- [02:00] David explains how CyberWire grew from a daily news brief into a full podcast network covering cybersecurity.
- [04:21] David recalls his background in media, theater, and early computer culture that shaped his path.
- [05:52] We hear how luck, timing, and technical skills combined to make podcasting a success for him.
- [07:17] David shares why he believes AI is the biggest change to cybersecurity in the past decade.
- [08:00] He notes that bad grammar is no longer a reliable phishing red flag thanks to large language models.
- [10:11] We discuss how phishing awareness training must adapt to more convincing scams.
- [12:30] He reflects on the unexpected rise of ransomware compared to early predictions about cryptomining.
- [14:08] David explains how ransomware groups now operate like corporations with support teams.
- [16:00] He raises concerns about ransom payments funding overseas criminal networks in Russia and North Korea.
- [18:15] We learn how scammers use call centers and human trafficking to scale their operations.
- [19:30] David describes current scam trends, including fake toll violation texts and AWS account alerts.
- [21:32] He points out how romance scams thrive on social media platforms like Facebook.
- [22:16] David recounts a frightening call where his mother was nearly scammed by criminals posing as bank security.
- [25:09] He emphasizes how scammers manipulate victims to stay locked into the story and ignore warnings.
- [26:03] We hear how criminals pressure victims into withdrawing cash, buying gold, or handing funds to unwitting couriers.
- [27:00] David shares a case where a delivery driver was tragically killed after being caught up in a scam pickup.
- [29:00] He talks about his own experiences of being scammed, including a Facebook credential-harvesting attempt.
- [32:08] David recalls falling for an “out of gas” roadside con and explains why he still prefers trusting people.
- [34:00] He reflects on how vague scam messages exploit imagination and insecurities.
- [36:08] We hear examples of scams that exploit real-life contexts, such as HR benefits or package deliveries.
- [37:45] David explains his current vigilance with real estate transactions and wire transfer fraud.
- [39:26] He predicts the next wave of scams will be evolutions of what already works, boosted by AI.
- [40:07] David outlines the persistence of “treasure box” and inheritance scams dating back hundreds of years.
- [41:02] He shares his hope that future AI “agents” will act as a safeguard for vulnerable users.
- [42:21] David speculates about “nuisance ransomware” that charges small amounts to fly under the radar.
- [43:25] He jokes about calling it “inconvenienceware” and wonders if such a niche could emerge.
- [44:39] David directs listeners to CyberWire.com to explore his podcasts and resources.
Thanks for joining us on Easy Prey. Be sure to subscribe to our podcast on iTunes and leave a nice review.