How Long Contexts Fail | Drew Breunig

The arrival of million-token context windows felt transformative. The ability to throw everything an agent might need into the prompt inspired visions of superintelligent assistants that could access any document, connect to every tool, and maintain perfect memory.

But as we’ve seen, bigger contexts create new failure modes. Context poisoning embeds errors that compound over time. Context distraction causes agents to lean heavily on their context and repeat past actions rather than push forward. Context confusion leads to irrelevant tool or document usage. Context clash creates internal contradictions that derail reasoning.