The Context Window Cliff: Application-Level Strategies for Long Conversations
A 90-minute support session. A research assistant that's been browsing documents for an hour. A coding agent that's touched a dozen files. All of these eventually hit the same wall — and when they do, they don't crash loudly. They get dumb.
The model starts forgetting what was decided twenty minutes ago. It contradicts itself. Retrieval results that should be obvious go missing. Users notice something is off but can't articulate why the assistant got worse. This is the context window cliff: not a hard error, but a gradual quality collapse that your monitoring almost certainly doesn't measure.
Expanding the context window doesn't fix this. Models with million-token windows still degrade on content in the middle, and even when they don't, you're paying for 100x more tokens while the model attends to a fraction of them. The solution is application-level context management — deliberate strategies for what stays in the window, what gets summarized, and what lives outside it entirely.
