Most practitioners can feel when a task is too large for an agent. A feeling does not help you decide what to do next. The failure it predicts is specific. Research analyzing more than 3,100 agent trajectories found that agents make "early myopic commitments that are systematically amplified over time and difficult to recover from," and that once an agent commits to a shallow plan in its first few decisions, recovering that trajectory is effectively impossible without a restart (complexity estimation write-up). That is the mechanism behind the vague signal: the agent did not run out of tokens, it ran out of scope and chose a plan that could never have finished the job.
The second mechanism is simpler. Even large context windows degrade before they are full, with accuracy dropping by tens of percentage points when relevant material sits in the middle of the window rather than at either end (same analysis). An agent working through twenty files is not just spending more tokens, it is reading its own earlier work through a fog.
So the useful question is not whether the task is big. It is how many countable things the agent must hold at once. Four counts cover most of it: files touched, branch decisions, tool calls, and the loop length of the test it must pass. Each is easy to estimate from the ticket before a single token is spent.



