Who Patches While You Sleep?

Play video

The signals

• Tim: The effort math that kept old code safe doesn't hold anymore. For decades, some software was left alone because finding the exploit "just wasn't worth the effort." PHP has run the web for over twenty years, and its latest flaws went public on October 21 after a private disclosure of at least 30 days, which "still wasn't in time for pretty much most of the internet." Agents can now scale up and scale out against one target, so patching will always run behind. His read: the new standard procedure is containment, and "get ready for rolling internet blackouts."
• Sam: The web was built for human effort, and bots don't know when to back off. A lot of the web's protection was the assumption that "it's too much work to do this, nobody would ever do this." Bots would, and since this spring they're more than half of internet traffic. Without protocols for doing it "the polite way," an agent that keeps trying "looks a lot like a DDoS attack," whether or not it is one.

The subtractions

• Tim: Himself, as the bottleneck on every patch. On the day the PHP flaws landed he checked his own AI security stack and found most of it "was not operational," with "no notification, no transparency, no visibility." Now he gets a daily report of what he runs and what's patchable, and is working out which updates an agent may apply on its own: his Mac's operating system, no; "PHP, definitely." His second subtraction is industry-wide: long-lived API tokens with coarse scope and no expiry, which are "such a pain in the butt to change" that nobody does.
• Sam: Security through obscurity. Old projects behind a simple password nobody would think to guess got by because the odds were in our favor. "Now there's bad things happening all the time." Anything without a real authentication method behind it comes out of his stack.

About this episode

Signals & Subtractions' first in-person session, recorded at Tim's place in Santa Rosa between his work calls. Tim is a Regional Field CTO at DigiCert, where he works with customers on PKI and the changes coming to it.

The middle of the conversation was about how much authority we hand an agent. Sam's version: he might ask someone he'd just met to watch his stuff while he runs to the market, but he wouldn't hand over every key and bank account and leave for an hour. Tim's answer was scope, bound tightly to identity and policy, "and hopefully cryptographically." Visibility was where everyone started at the end of 2025, and it leaves us reactive.

Tim's first step after the PHP news was an inventory: every system he runs, its version, and whether there's a newer one. That's a software bill of materials, which some medical devices already have to carry and most of us never keep. Step two was deciding what to do about it without being the reason nothing gets updated overnight.

One thing to do this week: pick one AI tool your team runs and run a check on it. Leave it in report-only for two weeks before it's allowed to change anything, and rotate its keys while you're there, "just for practice."

Links from the episode:

• Daily Patch Loop: Tim's daily security check for the tools, apps and repositories we run, which he ran on his own setup first
• The Report-Only Fortnight: this episode's takeaway built directly on the Daily Patch Loop, two weeks of reports before any agent may act
• The Vendor Update Card: six questions for a vendor about how its product changes after we've signed
• Tim McAllister: timmcallister.io, Substack, Medium, X
• Nate B. Jones's newsletter, where Sam and Tim met in the comments

Want to bring your own signal and subtraction? Find yours.

The method from this episode is one page with its copy-paste prompt and schema: The Report-Only Fortnight and The Vendor Update Card, linked under the decision above. Every takeaway.