Security | Threat Detection | Cyberattacks | DevSecOps | Compliance

ChatGPT Oopsies Series of Information - The 443 Podcast - Episode 356

This week on the podcast, we cover a Politico report detailing a security lapse at CISA in the United States involving sensitive data and a public version of ChatGPT. Next, we dive into a couple of recently resolved vulnerabilities in the SolarWinds Web Help Desk application. Finally, we end with some closure on a story about two Coalfire penetration testers who were arrested several years ago for completing a penetration test in Iowa.

Security Simplified: Endpoint Protection Made for Everyone

Attackers continue to move faster, automate more aggressively, and operate with greater precision at the endpoint. Detection alone is no longer enough. Security teams need clarity, context, and the ability to act decisively as threats unfold. Yet many endpoint approaches still rely heavily on manual investigation and response workflows that require human intervention. The result is alert overload, delayed response, increased operational effort, and growing pressure on already-stretched security teams.

Zero Trust for Data Privacy: The Backbone of Modern Cybersecurity

Data privacy used to be the realm of hospitals, banks, and fervent devotees of the Fourth Amendment to the US Constitution. Something we knew we wanted but conceptually assumed wouldn’t affect most people. Our dependence on the Internet for almost all aspects of daily life has changed that. In 2026, data privacy and cybersecurity are deeply intertwined. Protecting sensitive information isn’t just about stopping hackers.

Proud to be Data Privacy Week 2026 Champions with the National Cybersecurity Alliance

We are proud to be Data Privacy Week 2026 Champions with the National Cybersecurity Alliance. Stay tuned all week as we share practical tips, real-world insights, and expert perspectives from our teams and special guests across WatchGuard Tech All-Stars. A few simple reminders to start: Privacy is about choice, awareness, and control. And it starts with the everyday decisions we all make online.

The SMB Paradox: Most Targeted, Least Prepared for Cybersecurity

For years, the prevailing myth among small and midsize businesses (SMBs) was that they were too small to be a target. That myth has been definitively shattered. The reality is sobering: SMBs now account for a disproportionate share of cyber incidents and data exposure. In fact, research cited in the Guardz 2025 SMB Cybersecurity Report found that 43% of U.S. SMBs have experienced a cyberattack, including 27% hit within the past year.

Data Privacy: How Organizations Protect the Workplace From AI Threats

Data privacy in the workplace is not just compliance. It is how an organization protects employees, builds trust, and reduces business risk. Employees handle most workplace data, which makes them a major target for AI-powered threats like deepfakes and business email compromise (BEC). The best way to protect data is a mix of practical employee habits, realistic training, and strong controls like least privilege access, MFA, monitoring, and email authentication.

Zero Trust for Mid-Market: Why Modern IT Security Assumes Attacks Will Succeed

Guest post by WatchGuard Tech All-Star, Marko Bauer It's Monday morning, 7:30 AM. Your employees arrive at the office and can't log in. Systems are dead. Your phone rings. IT reports: Ransomware. All data encrypted. Then the email: €500,000 ransom. In 48 hours, the attackers will begin publishing customer data, contracts, and internal documents on the dark web. The first dump is already online, as “proof.” Your company is paralyzed. Production can't work. Sales has no access to orders.

From Alerts to Action: Automating Your MSP Security

As MSPs push for higher margins and tighter security outcomes, disconnected PSA, RMM, and security tools create noise, manual work, and missed opportunities. Deep, practical integrations are now the difference between a scalable managed security practice and an overloaded team. In this webinar, WatchGuard will show how our integrations with ConnectWise and Autotask help you.

You Don't Need 20 Different Perimeters. You Need One Identity Fabric.

Guest post by WatchGuard Tech All-Star, Michael Carter II At a glance: The trend is hard to ignore: most attackers do not “break in” anymore; they sign in using stolen or abused identities, not by bypassing a next-gen firewall, your EDR, or those fancy email and collaboration tool defenses. If an unauthorized identity can export it, you have not protected it, no matter how many controls you have in place.

Effective Response: A Key Factor in Your Reputation as an MSP

In cybersecurity, incidents test more than just technical resilience ‒ they also test trust. As a managed service provider (MSP), the preventive measures you implement are critical. However, the strength of your support during your clients’ most critical times is what truly defines the trust they have in you. A cybersecurity incident may be precisely the moment when your client evaluates whether you are delivering on your promises as a quality partner for their business.