The Defender’s Dilemma
10-5-2026 (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, October 5, 2026, and we’re back after a week on the road.
The Defender’s Dilemma
Last week, the UK’s National Cyber Security Centre (better known as the NCSC) had a very interesting blog post from their CTO for Architecture, Dave Chismon, called “One does not simply defend agentically.”
I thought it did a very nice job of laying out the Defender’s Dilemma, often attributed to security researcher Halvar Flake, who notes “All offensive problems are technical problems, and all defensive problems are political problems”.
For example, attackers might wonder ‘Do I have an exploit for this vulnerability?’ or ‘How do I avoid detection?’ while defenders may need to ask ‘Can we get budget to replace this end-of-life system or invest in a more secure option?’ Or ‘How do I get IT operations to make time for patching?’
This illustrates one of the core challenges around improving defenses using AI - in many ways, they’re not technical problems, so they don’t need (or even benefit from) technical solutions.
In typical NCSC fashion, there’s a robust framework built out in the article to help guide decision making, but it also points to some external resources on why this remains hard and how we can get better. Microsoft’s recent Digital Defense Report confirms that attackers are ahead in terms of benefitting from AI.
It boils down to something that I think we all know but maybe haven’t verbalized: the asymmetry in the cost of being wrong. I wish I could take credit for this, but it’s from Florian Roth’s post about the same issue, encouraging us to rationalize these things in a way that doesn’t hamstring us.
Indeed, the other cited sources encourage us to see these resources as “cattle, not pets,” meaning they’re not precious and are eminently replaceable. The original frame is referring to Kubernetes clusters (as opposed to named servers), though I’m struck that in an AI world, we would probably do well to consider the same for our agents.
In his post announcing that he’s joining Cognition (the company behind AI coding platform Devin), Alex Stamos (he formerly of SentinelOne and Facebook and Yahoo) wrote this:
“AI systems are software, they do not have rights, feelings or innate motivations”
Which I’m generally inclined to agree with. We’re all wrestling with an absolutely massive rate of change, and could do with a bit of updating our own priors in ways that will continue to serve us in this new world.
Fundraising
From a fundraising perspective, another strong week, with more than $17B in newly committed capital (just like two weeks ago), led by:
TPG raised $10b for a second climate-focused PE fund, per Bloomberg; and
Ares Management raised $4.2b for a new PE secondaries strategies fund.
The Wall Street Journal has a headline out today called “Private Equity Has a Problem,” though after reading the (short) article, it sounds like they’ve got the same challenge everyone else has: companies (and valuations) have largely right-sized coming out of COVID, leaving upside growth relatively limited in a frothy market.
What else is new?
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://www.ncsc.gov.uk/blogs/one-does-not-simply-defend-agentically
https://www.nextron-systems.com/2026/08/12/why-defensive-ai-has-a-harder-job-than-offensive-ai/
https://www.kubermatic.com/blog/cloud-native-best-practices-2-why-cattle-not-pets/
https://www.linkedin.com/pulse/why-im-joining-cognition-alex-stamos-bvlyf/
https://www.wsj.com/finance/investing/private-equity-has-a-problem-2bccfa69