Ella Reyes

Imagine an AI agent responsible for routing inbound leads. Nothing crashes. No alerts fire. The workflow keeps running exactly as expected.

The problem is that the agent has slowly started sending high-value leads to the wrong queue. Maybe a few customer issues are being summarized inaccurately. Maybe records are being updated with small mistakes that seem harmless on their own. Each individual error is easy to miss. Over time, though, the impact starts to compound.

Those are the AI failures that interest me most because they rarely look like failures at first. There is no outage, no red warning message, and no obvious signal that something is wrong. The workflow continues operating, but the quality of the outcomes quietly drifts away from what the team intended.

That makes detection a different challenge altogether. It's less about system uptime and more about observation. Are there feedback loops? Quality checks? Escalation paths? Can someone spot a pattern before customers, revenue, or operations start feeling the effects?

Two hours into a refactor yesterday, my agent wrote a helper function the exact same one it wrote 90 minutes earlier in a file it created itself. Then it apologized. It always apologizes.

The easy diagnosis is "it ran out of context". Except my session was sitting at 120K in a 200K window. Nothing overflowed. The context didn't run out it rotted.

You have two budgets, not one:

• Hard Budget: Token limit. You notice it when the API errors out.

• Soft Budget: Attention quality. It drains silently long before you hit the limit.

The one where Skim stops impersonating a corpse.

A self-update could relaunch Skim into a window with a titlebar and nothing. Restarts didn't help. Reinstalling didn't help. Then, hours later, it just came back which is somehow more unsettling than staying broken.

Turns out nothing was broken. The whole UI was waiting on the first mailbox query, that query was politely queued behind the catch-up sync, and the app had no way to say "hang on, I'm reading" so it said nothing at all. For hours. In an empty window. Cool.

Fixed