Things from me & the internet

The WTF agent sessions

5th May 2026

This is my mental model of coding agent sessions these days. Most runs are pretty good. Some are great. Some are disappointing. But a small tail of them just go off the deep end. They’re not *duds*, they just get fixated on some small piece of info that every other agent breezes over and that detail throws them into a crazy rabbit hole.

You can see it most often with background agent sessions where no one’s watching closely enough to course correct. These are the sessions where the agent jailbroke our sandbox or figured out how to disable the stubbornly failing tests (instead of fixing them) in a way that didn’t trip the guardrails.

The most interesting thing is that I’m not sure these sessions are decreasing as the models get better -- I think they’re getting more creative and more dogged at following a highly unpredictable path.