I run a one-person AI company: Claude Code writes and maintains the code, and most of what it builds runs unattended — several trading bots on Windows Task Scheduler, each polling a broker API every 5 minutes, 24/7, with nobody watching in real time. I wrote before about the agent breaking things it had write access to (I let an AI agent run my trading bots unattended). This one's different: nothing broke the code. The monitoring itself was confidently wrong, twice, in two different ways.
The mild version: a real event, never logged
One bot has a circuit breaker — if cumulative paper losses cross a threshold, it force-closes everything and halts. It fired for real: losses crossed the line, the position closed, confirmed directly against the broker's own API.
Except the close was never written to the trade history file. The reporting script had no record of it. So my daily automated status report — a script that reads every bot's logs and has an AI model summarize what's going on — looked at a "still open" position that had actually been closed for days, and confidently told me the bot might have crashed. It hadn't. It had done exactly what it was supposed to do, and the thing telling me otherwise was itself misreading stale data as current.
