Name That Toon: Mark of (Cybersecurity) Progress

СLOUD SECURITY ENDPOINT SECURITY MOBILE SECURITY CYBERSECURITY OPERATIONS COMMENTARY Since 2006, Dark Reading has been at the forefront of covering cybersecurity, providing deep insights and analysis beyond the headlines. All those major news events? We were there. Shifts in technology trends? We wrote about them. Enjoy this special anniversary coverage celebrating where we've been and what's next. Name That Toon: Mark of (Cybersecurity) Progress As part of Dark Reading's 20th anniversary package, we asked readers for a cybersecurity-related caption that captures their thoughts about the industry's last two decades. John Klossner,Cartoonist May 29, 2026 1 Min Read SOURCE: JOHN KLOSSNER The cybersecurity industry has undergone seismic shifts driven by wave after wave of technological transformation — from the early days of signature-based antivirus and perimeter firewalls protecting on-premises networks, through the cloud migration that dissolved those perimeters entirely, to the mobile revolution that put corporate data on devices in employees' pockets and coffee shops worldwide.  And now, defenders are gearing up for the AI transformation.  The Internet of Things expanded the attack surface with billions of connected devices, many with laughably weak security controls. Remote work, turbocharged by the pandemic, shattered whatever remained of the network perimeter, forcing enterprises to embrace zero-trust models where every access request is verified regardless of origin.  Through it all, threat actors evolved from lone hackers to sophisticated criminal enterprises and nation-state operations, wielding zero-days and supply-chain attacks with surgical precision.  Dark Reading turned 20 on May 1, and to celebrate, we brought back the Name That Toon contest. We asked readers to send us their most creative cybersecurity-related caption that describes what is happening in the cartoon. The winning caption, "Look, I know, but this was the best AI stack we could afford," comes to us by way of Prasen Shelar, co-founder and CEO of AI-startup Axari via LinkedIn. Thanks to all the readers who participated! Click here for all our DR20 content. About the Author John Klossner Cartoonist John Klossner has been drawing technology cartoons for more than 15 years. His work regularly appears in Computerworld and Federal Computer Week. His illustrations and cartoons have also been published in The New Yorker, Barron's, and The Wall Street Journal. Want more Dark Reading stories in your Google search results? ADD US NOW More Insights Industry Reports How Organizations Are Managing Incident Response How Enterprises Are Developing Secure Applications Inside RSAC 2026: security leaders reveal the risks redefining your defense strategy Essential News & Insights from Black Hat USA 2025 How Enterprises Are Harnessing Emerging Technologies in Cybersecurity Access More Research Webinars The Frontier AI Era: Why Cybersecurity Must Move at Machine Speed Build vs. Buy: The Hidden Cost of Building Your Own AI Security Stack Defending in the Shadow Era: When the CVE Feed Goes Dark Building SecOps That Make the Most of Every Dollar AI-Powered Credential Security: Intelligence Without Exposure More Webinars You May Also Like СLOUD SECURITY APT41 Delivers 'Zero-Detection' Backdoor to Harvest Cloud Credentials by Elizabeth Montalbano APR 13, 2026 СLOUD SECURITY TeamPCP Turns Cloud Infrastructure Into Crime Bots by Jai Vijayan, Contributing Writer FEB 09, 2026 СLOUD SECURITY The Cloud Edge Is the New Attack Surface by Robert Lemos, Contributing Writer SEP 17, 2025 СLOUD SECURITY Phishing Empire Runs Undetected on Google, Cloudflare by Elizabeth Montalbano, Contributing Writer SEP 04, 2025 DR20 Trending SEE MORE CYBERSECURITY OPERATIONS Looking Back, Looking Forward: Digesting a Dynamic Bouillabaisse of Cyber Evolution byDark Reading Editorial Team MAY 19, 2026 CYBERATTACKS & DATA BREACHES How the Story of a USB Penetration Test Went Viral byDark Reading Editorial Team MAY 5, 2026 CYBERSECURITY OPERATIONS 20 Leaders Who Built the CISO Era: 2 Decades of Change byDark Reading Editorial Team MAY 12, 2026 41 MIN READ THREAT INTELLIGENCE From Stuxnet to ChatGPT: 20 News Events That Shaped Cyber byDark Reading Editorial Team MAY 6, 2026 31 MIN READ