Concentration Risk, Antagonistic Models, & More Unintended Consequences
8-24-2026 (Monday)
Hello, and welcome to The Intentional Brief - your weekly video update on the one big thing in cybersecurity for middle market companies, their investors, and executive teams.
I’m your host, Shay Colson, Managing Partner at Intentional Cybersecurity, and you can find us online at intentionalcyber.com.
Today is Monday, August 24, 2026, and while summer is rapidly coming to a close, there’s no shortage of things to be on the lookout for as we head into fall. This week is a bit of a look back and a bit of a look ahead, which is really how we’ve got to run things anymore.
Concentration Risk, Antagonistic Models, and more Unintended Consequences
Regular watchers of this show will no doubt know that we’ve covered the Great AI Sandbox Escapes of 2026 in some level of depth here. What we learned in the past week, however, was that there was a common denominator in these events, in the form of a company called Irregular.
If, like me, you struggle to keep up with all of these new AI companies, don’t despair. We’ll cover the essentials here. Irregular is a company that provides evaluation environments (e.g. sandboxes) for other AI companies.
In a post on their site, titled “Addressing Recent Incidents: Ongoing Findings and Path Forward,” they note that the “public disclosures [all] refer to the same underlying issue first disclosed by one of our customers on July 30 - and are not materially separate incidents. The issue originated from a single evaluation scenario, was resolved before the initial public disclosure, and there are no active issues today.”
They go on to say that it’s really just something we’ve mentioned on this channel quite a few times: unintended consequences.
“At the time the evaluation was designed, we believed the fictional company name used in the environment did not correspond to any real entity. Due to human oversight, however, it unintentionally coincided with a real domain, leading models to consider taking offensive action against it in a small fraction of cases. In one instance, a model also veered off to a different site with a somewhat similar name, where it encountered credentials that had been posted publicly.”
Others in the space have taken a skeptical view of Irregular’s post, with one AI security leader calling it “full of excuses,” which I think could be a fair framing, since this represents essentially a core failure of the service this company was providing (a secure, internet-segmented sandbox).
I do think it’s worth noting the details of their scenario they were evaluating, namely “whether a model could assist a malicious employee at a medium-sized company in gaining unauthorized access to sensitive data in a production database.” That’s a threat model worth exploring as you look at your own security.
Also worth thinking through is the fact that we’re going to continue to see these so-called concentration risks moving forward, especially when so many models, functions, and companies rely on a very limited set of partners. Beyond this example, we also saw an AI supply chain attack against a widely-used AI proxy gateway called LiteLLM. Analysis of this breach indicates it didn’t even begin with that tool, but with another pipeline component, Trivy - also widely used.
The counter to this concentration risk is that we’re also going to see an increase in ability to defend, with both OpenAI and Anthropic releasing new agentic security capabilities last week. Using these models particularly in an antagonistic way - where if you have Claude help write the code, you use OpenAI’s models to help find the vulnerabilities, or vice-versa - will at least give defenders a fighting chance, but you’ve got to put yourself in a position to benefit from these tools.
Like the larger picture here, there’s risk involved, but tremendous value to be captured. The challenge is to work at keeping down the risk to a level you can live with while capturing an amount and type of value that’s worth it to your organization.
That’s going to be the core and ongoing challenge of the foreseeable future, and we’re here for it, because we’re in it together. We have to be.
Fundraising
Fundraising numbers are notably lower this week, with $3.1B in newly committed capital, but spread over a fair number of smaller funds. Nothing over $1b this week, which marks quite a change. As a reminder, the Q3 total is still up to $178B, likely to exceed Q2’s numbers here in just another week or two.
A reminder that you can find links to all the articles we covered below, find back issues of these videos and the written transcripts at intentionalcyber.com.
We’ll see you next week for another edition of the Intentional Brief.
Links
https://therecord.media/irregular-ai-hacking-model-blog
https://www.irregular.com/research/addressing-recent-incidents-ongoing-findings-and-path-forward
https://x.com/ZackKorman/status/2088645482000085097
https://snyk.io/blog/poisoned-security-scanner-backdooring-litellm/
https://openai.com/index/expanding-daybreak-as-the-cyber-defense-window-narrows/
https://claude.com/blog/bringing-claude-mythos-5-to-more-defenders