DarkReading-Features Edition

"20 years in cyber:  DarkReading marks milestone with month of special coverage."

Views expressed in this cybersecurity, cyber crime update are those of the reporters and correspondents.  Accessed on 30 May 2026, 1609 UTC.

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Russ Roberts (https://www.hawaiicybersecurityjournal.net).

May​ 30,​ 2026

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Features Edition

This week’s insights for cybersecurity professionals

NOTE FROM THE EDITOR Welcome to this special issue of the Dark Reading Features Edition newsletter. You will find our unique collection of content celebrating two decades of cybersecurity news, technology, trends, and industry luminaries. Please also visit our dedicated Dark Reading 20 page.  Happy (Dark) Reading!   Kelly Jackson Higgins Editor-in-Chief, Dark Reading Email

20 Years in Cyber: Dark Reading Marks Milestone With Month of Special Coverage Dark Reading went live on May 1, 2006. We have a celebration planned that spans our two decades of covering the industry, and you, dear readers, are invited.

From Stuxnet to ChatGPT: 20 News Events That Shaped Cyber As part of its 20th anniversary celebration, Dark Reading looks back on 20 of the biggest newsmaking events from the past two decades that influenced the risk landscape for today's cybersecurity teams.

How the Story of a USB Penetration Test Went Viral [Podcast]: Dark Reading Confidential Episode 18 — Two decades ago Dark Reading posted its first blockbuster: a column by a pen tester who sprinkled rigged thumb drives around a credit union parking lot and let curious employees do the rest. This episode looks back at the history-making piece with its author Steve Stasiukonis, Dark Reading senior editor Becky Bracken, and Dark Reading's editor-in-chief Kelly Jackson Higgins.

Boulevard of Broken Dreams: 2 Decades of Cyber Fails From the MGM and Caesars fiasco and MOVEit's patch nightmare to epic business blunders and the jaded reality of living in a post-breach world, Dark Reading looks back at the mistakes, miscalculations, systemic failures, and cringeworthy moments that still have us shaking our heads.

Looking Back, Looking Forward: Digesting a Dynamic Bouillabaisse of Cyber Evolution In this latest installment of the Reporters' Notebook video series, Dark Reading editors reflect on two decades of dramatic change — from perimeter defense to assume-breach strategies — and warn that while AI, cloud, and COVID-19 have transformed the threat landscape, organizations are still failing at fundamental security hygiene that could stop sophisticated attacks in their tracks.

20 Leaders Who Built the CISO Era: 2 Decades of Change As part of Dark Reading's 20th anniversary special coverage, we profile the CISOs, founders, researchers, criminals, and policymakers who rewrote the enterprise risk playbook.

Cyber Pioneers Ponder Past as Prologue Robert "RSnake" Hansen, Katie Moussouris, Rich Mogull, Richard Stiennon, and Bruce Schneier reflect on how their favorite columns penned for Dark Reading over the past 20 years have stood the test of time.

Cybersecurity Evolution: How We Went From Perimeter Defense to AI-Native Security The cybersecurity industry of 2006 barely resembled today's billion-dollar behemoth. As part of Dark Reading's 20th anniversary celebration, we trace the industry's evolution through a technology lens.

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.

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Commentary

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Remembering Tim Wilson, Whose Legacy Lives on at Dark Reading The co-founder and former editor-in-chief passed away five years ago in November. As Dark Reading enters is third decade, we pause to celebrate and honor Wilson's instrumental role in building and elevating the media site.

How Dark Reading Lifted Off the Launchpad in 2006 Twenty years ago, this media brand didn't have a print edition to attract eyeballs and sponsors. Top-notch content and editorial talent did the heavy lifting.

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