Online Pandora’s Box for Contextual LLM Cascading

Motivated by Large Language Model (LLM) cascading, we propose an online contextual Pandora's Box model for adaptively querying and selecting LLM APIs. In each period, a decision-maker observes a request context and faces a two-phase decision problem. In the query phase, the decision-maker sequentially queries APIs, where each query reveals a generated output and the decision-maker incurs an (output-dependent) cost. In the selection phase, the decision-maker selects one of the generated outputs to deploy and observes only the downstream reward of the deployed output. This output-mediated feedback structure differs from classical online contextual Pandora's Box models, in which opening a box directly reveals its reward. Rather than estimating the full conditional output and cost distributions of each API, we directly model the reservation index and develop a learning approach for the query phase. Specifically, we impose a parametric structure on the contextual reservation index functions induced by the classical Weitzman's policy. Our Double Optimistic Weitzman’s (DOW) combines generalized method of moments (GMM) type estimation of these reservation indices with UCB-style confidence bounds for both these indices and the shared output-level reward evaluator. Under regularity conditions, we prove that the resulting policy achieves dimension-dependent $\widetilde O(\sqrt T)$ cumulative regret over a horizon of $T$ periods.