Dark Reading Turns 20: The Name That Toon Caption Contest Is Back
A cybersecurity cartoon contest is a low-stakes way to mark two decades of covering an industry that never stops generating material.
Twenty years is a long time in this industry. Threats that didn't exist when Dark Reading launched in 2006 — cloud misconfigurations, container escapes, LLM prompt injection — are now the bread and butter of every security team's weekly standup.
To mark the anniversary, the outlet is running a caption contest. Cartoonist John Klossner illustrated a scene meant to capture the evolution of cybersecurity from 2006 to 2026. The premise: what were practitioners thinking then versus now, and what are they saying?
The format is simple. Submit a caption by emailing the team with the subject line "Dark Reading 20 Toon", or drop your entry on LinkedIn, Facebook, BlueSky, or X. The editorial team picks a winner, who gets a $20 gift card and a public shout-out. The winning caption gets republished alongside the cartoon.
Honestly, the more interesting prompt here isn't the contest mechanics — it's the underlying question Klossner's cartoon is asking. The gap between 2006-era security thinking and where we are now is enormous. Back then, the conversation was firewalls and antivirus. Now it's IAM policy drift in AWS, lateral movement through over-permissioned GCP service accounts, and whether your CI/CD pipeline is quietly exfiltrating secrets through a compromised GitHub Action.
The tools changed. The failure mode — teams underestimating attacker creativity while overestimating their own detection coverage — has not.
If you're going to enter, the deadline is June 26, 2026. More details are available directly from the Dark Reading editorial team via the contact address above.
Operational takeaway: if your mental model of the threat landscape hasn't been updated since the Obama administration, the cartoon probably isn't the only thing that needs a new caption.
