Cyberside Chats: Cybersecurity Insights from the Experts

Why do so many major cyberattacks happen over holiday weekends? In this episode, Sherri and Matt share their own 4th of July anxiety as security professionals—and walk through some of the most infamous attacks timed to exploit long weekends, including the Kaseya ransomware outbreak, the MOVEit breach, and the Bangladesh Bank heist. From retail breaches around Thanksgiving to a cyber hit on Krispy...

In June 2025, the White House issued an executive order that quietly eliminated several key federal cybersecurity requirements. In this episode of Cyberside Chats, Sherri and Matt break down exactly what changed—from the removal of secure software attestations to the rollback of authentication requirements—and what remains in place, including post-quantum encryption support and the FTC’s Cyber Tru...

Forget everything you thought you knew about ransomware. Today’s threat actors aren’t locking your files—they’re stealing your data and threatening to leak it unless you pay up.  In this episode, we dive into the rise of data-only extortion campaigns and explore why encryption is becoming optional for cybercriminals. From real-world trends like the rebrand of Hunters International to “World Leaks,...

Can your AI assistant become a silent data leak? In this episode of Cyberside Chats, Sherri Davidoff and Matt Durrin break down EchoLeak, a zero-click exploit in Microsoft 365 Copilot that shows how attackers can manipulate AI systems using nothing more than an email. No clicks. No downloads. Just a cleverly crafted message that turns your AI into an unintentional insider threat.  They also share...

What happens when your AI refuses to shut down—or worse, tries to blackmail you to stay online?  Join us for a riveting Cyberside Chats Live as we dig into two chilling real-world incidents: one where OpenAI’s newest model bypassed shutdown scripts during testing, and another where Anthropic’s Claude Opus 4 wrote blackmail messages and threatened users in a disturbing act of self-preservation. The...

Retail breaches are back — but they’ve evolved. This isn’t about skimming cards anymore. From ransomware taking down pharmacies to credential stuffing attacks hitting brand loyalty, today’s breaches are about disruption, trust, and third-party exposure. In this episode of Cyberside Chats, hosts Sherri Davidoff and Matt Durrin break down the latest retail breach wave, revisit lessons from the 2013...

Think your network is locked down? Think again. In this episode of Cyberside Chats, we’re joined by Tom Pohl, LMG Security’s head of penetration testing, whose team routinely gains domain admin access in over 90% of their engagements. How do they do it—and more importantly, how can you stop real attackers from doing the same?  Tom shares the most common weak points his team exploits, from insecure...

What happens to your digital world when you die? In this episode of Cyberside Chats, LMG Security’s Tom Pohl joins the conversation to discuss the often-overlooked cybersecurity and privacy implications of death. From encrypted files and password managers to social media and device access, we’ll explore how to ensure your loved ones can navigate your digital legacy—without needing a password-crack...

In this explosive episode of Cyberside Chats, we dive into one of the most shocking developments in ransomware history—LockBit got hacked. Join us as we unpack the breach of one of the world’s most notorious ransomware-as-a-service gangs. We explore what was leaked, why it matters, and how this leak compares to past takedowns like Conti. You'll also get the latest insights into the 2025 ransomware...

Cybercriminals are exploiting outdated routers to build massive proxy networks that hide malware operations, fraud, and credential theft—right under the radar of enterprise defenses. In this episode, Sherri and Matt unpack the FBI’s May 2025 alert, the role of TheMoon malware, and how the Faceless proxy service industrializes anonymity for hire. Learn how these botnets work, why they matter for yo...

AI isn’t just revolutionizing business—it’s reshaping the threat landscape. Cybercriminals are now weaponizing AI to launch faster, more convincing, and more scalable attacks. From deepfake video scams to LLM-guided exploit development, the new wave of AI-driven cybercrime is already here.  In this engaging and eye-opening session, Sherri and Matt share how hackers are using AI tools in the wild—o...

Quantum computing is advancing rapidly—and with it, the potential to break today’s most widely used encryption standards. In this episode of Cyberside Chats, Sherri and Matt cut through the hype to explore the real-world cybersecurity implications of quantum technology. From the looming threat to encryption to the emerging field of post-quantum cryptography, our experts will explain what security...

CISA, the U.S. government’s lead cyber defense agency, just took a major financial hit—and the fallout could affect everyone. From layoffs and ISAC cuts to a near-shutdown of the CVE program, these changes weaken critical infrastructure for cyber defense. In this episode of Cyberside Chats, we unpack what’s been cut, how it impacts proactive services like free risk assessments and scanning, and wh...

When a company built on sensitive data collapses, what happens to the information it collected? In this episode of Cyberside Chats, we examine 23andMe’s data breach, its March 2025 bankruptcy, and the uncomfortable parallels with the 2009 Flyclear shutdown. What happens to biometric or genetic data when a vendor goes under? What protections failed—and what should corporate security leaders do diff...

Unauthorized communication platforms—aka shadow channels—are increasingly used within enterprise and government environments, as demonstrated by the recent Signal scandal. In this week's episode of Cyberside Chats, special guest Karen Sprenger, COO at LMG Security, joins Matt Durrin to delve into the critical issue of shadow IT, focusing on recent controversies involving unauthorized communication...

Governments are pushing for encryption backdoors—but at what cost? In this episode of Cyberside Chats, we break down Apple’s fight against the UK’s demands, the global backlash, and what it means for cybersecurity professionals. Are backdoors a necessary tool for law enforcement, or do they open the floodgates for cybercriminals? Join us as we explore real-world risks, historical backdoor failures...

AI-generated deepfakes and voice phishing attacks are rapidly evolving, tricking even the most tech-savvy professionals. In this episode of Cyberside Chats, we break down real-world cases where cybercriminals used deepfake videos, voice clones, and trusted platforms like YouTube, Google, and Apple to bypass security defenses. Learn how these scams work and what IT and security leaders can do to pr...

Recent telecom breaches have exposed a critical security risk for businesses everywhere. Nation-state hackers and cybercriminals are stealing metadata, tracking high-profile targets, and even intercepting calls—all without breaking into corporate networks. In this episode, we analyze major telecom hacks, including the Salt Typhoon breach, and share practical strategies for IT leaders to protect th...

The March 2025 Microsoft Outlook outage left thousands of organizations scrambling. But this wasn’t just an isolated event—recent outages from CrowdStrike, AT&T, and UK banks highlight the systemic risks businesses face. In this episode, we break down the latest Microsoft outage, discuss its impact on cyber insurance, and provide actionable steps to help organizations reduce the risk of busine...

Do you think your old cloud storage is harmless? Think again. This week on Cyberside Chats, Sherri and Matt dive into shocking new research from Watchtowr that reveals how hackers can take over abandoned Amazon S3 buckets—and use them to infiltrate government agencies, Fortune 500 companies, and critical infrastructure. We’ll break down real-world examples of how this risk can be exploited, includ...

In this episode of Cyberside Chats, we dive into the world of ransomware, focusing on the notorious Ghost Ransomware Gang. Recently flagged by the FBI and CISA, Ghost has targeted organizations in over 70 countries. We explore their methods of infiltration, with a spotlight on outdated software vulnerabilities, and discuss how organizations can fortify their defenses. We'll also provide insights i...

Zero-day exploits are hitting faster than ever—are you ready? This week, we dive into the U.S. Treasury breach, which we now know involved multiple zero-days, including a newly discovered flaw in BeyondTrust’s security software. Attackers aren’t just targeting IT systems anymore—they’re coming for security tools themselves to gain privileged access.  We also cover new zero-days in Microsoft, Apple...

In this episode of Cyberside Chats, Sherri and Matt dive into a shocking new cybersecurity controversy at the Office of Personnel Management (OPM). A rogue email server, installed outside normal security controls, has raised alarms about data security risks to millions of federal employees. We compare this developing situation to the infamous 2015 OPM hack, in which state-sponsored attackers stole...

DeepSeek or DeepRisk? A new AI powerhouse is making waves—DeepSeek has skyrocketed in popularity, rivaling top AI models at a fraction of the cost. But with data stored in China and unknown security safeguards, is your organization at risk? In this episode of Cyberside Chats, Sherri Davidoff and Matt Durrin break down the cybersecurity implications of AI tools like DeepSeek. You'll learn about: ▪...

In this episode of Cyberside Chats, we dive into the surprising pardon of Ross Ulbricht, creator of the infamous Silk Road dark web marketplace. What does this decision mean for the future of cybercrime enforcement and your organization’s security? We’ll explore the potential policy shift, how it could embolden criminals, and actionable steps you can take to stay ahead of evolving threats. Don't m...