August 25, 2026

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It’s Tuesday! With back-to-school shopping in full swing, it’s a good time to consider the staple items your IT department needs. We suggest adding some whimsy with pet-themed notebooks and folders.

In today’s edition:

🤖 Prompting bad

🧍 Standing around

💲 Wasted spending

—Billy Hurley, Brianna Monsanto

CYBERSECURITY

Setting traps

Francis Scialabba

If you thought training a human employee to resist social engineering was hard, just wait until you try the same thing with an AI bot.

Threat-intelligence team Cisco Talos recently found that cyber adversaries are getting good at tricking large language models (LLMs) into engaging in nefarious activities like revealing sensitive data. The bots seem particularly susceptible to adversarial prompts disguised as cybersecurity testing.

“We did not encounter any sophisticated encoding or techniques designed to trick the models—most of the time it was a simple, ‘I’m allowed to do this,’ and the model complied,” the team wrote in its August 4 post.

After examining real-life adversarial prompts (featuring more use of “bro” than you might expect), the researchers learned that bot guardrails can be sidestepped with user claims such as being on a bug-bounty mission.

More on tricking LLMs.—BH

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SOFTWARE

Stand up for yourself

Getty Images

Lokesh Karanam’s update to the team used to be one sentence:

I’m working on ticket number 100. I am working on creating a tracking UI, and everything is going well.

That’s how a “standup”—a standard developer check-in—was meant to be, after all: a quick, right-down-the-line progress update short enough to spare everyone from having to sit down.

These days, as staff software engineer at marketing and business-services firm RRD, Karanam leads the daily meetings, but leaves more room for updates than in the past. The 13 or so developers and product managers arriving from different time zones onto the morning call are encouraged to give everyone a more comprehensive view of their workload. Karanam himself, in his work summaries, describes his situation, the task he’s responsible for, actions taken, and their result—a “STAR” method that takes at least a paragraph to go through.

The art of a tight meeting.—BH

IT STRATEGY

Cost of ownership

An AI sparks icon covered in price stickers

Morning Brew Inc.

There are good surprises, bad surprises…and then there’s AI surprises.

The lattermost is all too common, according to a new report from Harness, which found that almost three-fourths (72%) of companies experienced a surprise bill or an unexpected spike in AI costs within the past year. (The findings were based on a survey of 700 global FinOps and engineering leaders.)

Unexpected costs aren’t the only thing emptying enterprises’ pockets. Harness found that a little over one-quarter (26%) of overall AI spend is wasted. To put that into perspective, that’s about $130,000 down the drain for companies with a monthly AI budget of $500,000.

The visibility issue. In its report, Harness said surprise AI bills and wasted spend are byproducts of three structural issues within companies. One is gaps in visibility, which Harness’ FinOps Advisory Director Patrick Brogan told IT Brew is partly driven by provider sprawl as organizations tap multiple AI providers at once for services.

Here’s the root of the issue.—BM

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patch notes

Francis Scialabba

Today’s top IT reads.

Stat: Over 500. That’s how many organizations have been impacted by Medusa Ransomware over the past five years. (Cyber Magazine)

Quote: “Without the knowledge of what risks could exist with skills, you’re kind of operating blind.”—Omar Turner, a managing director of cloud and AI security projects at Microsoft, said of a new list of the top security issues for AI agentic skills (Dark Reading)

Read: An AI agent for everything? (TechCrunch)

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Written by Billy Hurley and Brianna Monsanto

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☕ Guardrails interrupted