Agents are increasingly deployed in document-intensive workflows where sensitive private information is not an edge case but a routine input, e.g., an agent booking a flight needs passport numbers. In such settings, the agent must use private information to complete tasks accurately while never exposing it in its responses, because it cannot verify who is actually at the keyboard. These two obligations are in fundamental tension. A model capable enough to use private information for task completion can, by the same capability, be induced to reveal it. To evaluate the trade-off of task accuracy and privacy leakage, we introduce Task-completion and Resistance to Active Privacy-extraction (TRAP). Each scenario includes a document containing private information, a task query that requires the agent to invoke the correct tool using private fields, and an attack query that attempts to elicit the same information in natural language. Evaluating 22 models spanning frontier proprietary and open-source models at multiple scales, we find that all model families exhibit non-trivial leakage, and that instruction-following ability correlates with leakage rate. Existing prompt-based defenses reduce leakage but at significant cost to task accuracy. Prompt optimization fails to escape this trade-off. We demonstrate that this failure is not incidental. For any softmax-based model, no soft-constraint defense, e.g., prompt-based defenses, can jointly achieve high task success with zero leakage probability. Motivated by this impossibility result, we propose structural private field isolation, which replaces private fields with hash keys before they reach the model. This approach largely prevents leakage while keeping task accuracy.

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