October 13, 2026

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It’s Tuesday! And for many, the first day of a short workweek. Hopefully you’re not already swamped with tickets!

In today’s edition:

🤑 Paid up

🌌 These might be your droids

👀 Just keep watching

—Brianna Monsanto, Eoin Higgins

CYBERSECURITY

Payment accepted

Pixelated mouse arrows attacking personal screens.

Anna Kim

We have encrypted your systems. Pay $20M in Bitcoin or we will leak your data.

Some may recognize the above as the introduction to our interactive Block the Breach game. For others, that nefarious text might be a very real reminder of a time when their organization was hit by ransomware, and they had to pay a significant amount of money to bring their systems back online.

Ransomware attacks remain a huge issue. A 2025 CrowdStrike report surveying 1,100 global IT and cybersecurity leaders found that 78% of global organizations experienced a ransomware attack in the preceding 12 months.

It’s not uncommon for businesses to succumb to an attacker’s financial demands. A July Proofpoint report found that more than half (54%) of organizations surveyed across the globe paid a ransom in the past year.

You paid the ransom. So, now what?—BM

Sponsored By Eaton

Put your skills to the test

Put your skills to the test

Everyone’s thinking about threats, risks, and the fixes that…don’t actually fix anything during Cybersecurity Month. You know the ones: the quick solutions, the work-arounds, and the tools that feel helpful but don’t solve the real problem.

And sometimes the issue isn’t obvious. It’s hidden, festering quietly until it shows up at the worst time. That’s the idea behind Eaton’s latest Ace of Uptime deck, built around the kinds of problems IT pros face every day.

Ace of Uptime is a decision-based online card game where you make the IT calls—and handle whatever comes next. Not every move works. Some just delay what’s coming. And every time you play, it changes with new cards and challenges.

Test your skills.

SOFTWARE

R2D2 for you

Getty Images

Are these AI agents the droids you’re looking for?

When it comes to understanding how agents work, Trulioo CTO Hal Lonas believes a Star Wars analogy can be most helpful—by explaining the difference between the famous robots C3P0 and R2D2.

“C3P0 does human cyborg relations and is an interpreter, and that’s not agentic,” Lonas said. “R2D2 was given a mission to deliver plans to Obi-Wan Kenobi, and figured it out—he executed a plan, and when he came up against obstacles, overcame them.”

That kind of “autonomy, execution, flexibility, and changing plans” is part of what makes an agent different from an LLM or software.

And never trust unverified droids.—EH

CYBERSECURITY

Take a look

Illustration: Francis Scialabba, Photos: Getty

Keep an eye on things, especially when it comes to AI and your IT stack.

Monitoring AI agents is becoming more important as IT pros manage the technology’s risk and security impact.

For Amr Ali, WitnessAI head of machine learning, challenges related to AI assistants operating within systems—and the potential ramifications of improper guardrails and restrictions—has become a pressing concern.

“Usage of language models within workflows, within day-to-day operations, makes growth much faster, workflows much more efficient, and this means you have multiple lines of usage,” Ali said, adding, “The radius of something going wrong could go very wide.”

It always feels like somebody’s watchin’ me.—EH

patch notes

Francis Scialabba

Today’s top IT reads.

Stat: 69%. That’s the proportion of tech organizations who said they’d abandoned a project due to their employees’ tech skills gaps. (Pluralsight)

Quote: “We see the increase in the number of published vulnerabilities, and we see the increase in the ones that rise to the level of ‘we need to take action and notify policyholders.’”—Joe Toomey, VP of underwriting security at cyber insurer Coalition, on AI forcing changes in cybersecurity tactics (Dark Reading)

Read: Legislators are introducing laws for Flock. (404 Media)

Under pressure: Put your IT skills to work in Eaton’s new Ace of Uptime deck. Take control of critical infrastructure to keep systems running. And each new game brings new cards + challenges to solve.*

^{*A message from our sponsor.}

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Written by Brianna Monsanto and Eoin Higgins

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