When Is Delegated Play Truthful? Within-Range Regret and the Trilemma of Aligned Delegation

Advertisers delegate bidding to autobidders; users delegate tasks to language-model agents. A person describes what they want to an automated proxy that acts in a mechanism on their behalf. This is the revelation principle in production, and it forces a question classical theory assumes away: when is it optimal to describe yourself honestly to your own proxy? We show the answer turns on one quantity, the proxy's within-range regret. The most a principal can gain by misreporting equals the regret of the proxy's honest-report action against those the principal could have steered it to take. Honest self-description is optimal exactly when the proxy already plays the best action it can reach, that is, when it is loyal (Theorem 1). The identity unifies auction-specific autobidding results and pins down when the faithful-communication assumption behind language-model elicitation proxies (Huang et al.) holds. The identity constrains guardrails placed on proxies, from bid caps to a model's alignment layer. No guardrail can be at once binding (it displaces the truthful action from the proxy's best reachable outcome), truthful (honest reporting stays optimal), and capability-preserving (that outcome stays reachable through some report); any two preclude the third (Theorem 2). A safety constraint that alters what a model does while leaving its best output reachable makes honest description of intent suboptimal, so a sharper report can gain. This is the incentive behind prompt-engineering and jailbreaking. Because within-range regret is #P-hard to compute exactly, we estimate it from samples and maintain it as a model is updated, at a cost set by how far the model drifts, not how often it changes. Running it on production language models from five providers under an alignment-style cap, we find honest reporting leaves surplus unclaimed on every model, recovered by inflating the report.