5 Things That Break When You Run AI Agents Unsupervised (And How to Fix Them)

Running AI agents autonomously sounds like the dream: fire it off, go to sleep, wake up to done work. I've been doing exactly that for the past few weeks — agents running 24/7, checking emails, posting content, managing cron jobs, writing code. And I've catalogued every failure mode that actually bit me. Here are the 5 that matter: 1. The Cron Timeout Death Spiral I set up 4 cron jobs to run every 2-6 hours. Smart, right? Except my default session timeout was set to 300 seconds — and the tasks were taking 400. Result: every job would start, get 80% done, then silently die. No error. No output. Just... nothing. I'd check at midnight and discover 6 hours of "work" that produced zero results. Fix: Set your timeout generously ( timeoutSeconds: 1200 minimum for anything non-trivial). Monitor for silent failures, not just errors. 2. The Documentation Trap I asked an agent to "prepare the launch strategy." Three sessions later, I had 12 markdown files, 3 strategy docs, and a detailed 47-point