Cross-Entropy Risk Estimation for Language Models: Inconsistency Must Be Dense, and the Holdout Method Is No Exception

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arXiv:2608.15798v1 Announce Type: new Abstract: Language models are compared by their held-out per-token cross-entropy risk---the quantity scaling laws are fitted to. We show that it cannot be consistently estimated. Consistency, or convergence to the estimand, is defined relative to a \emph{possible state of the world}: a pair consisting of a data-generating distribution and a model we turn out to train. Quantifying over models as well as data-generating mechanisms is essential, because what decides whether a model's risk is estimable is a tail property of the distribution its weights induce, which no sample reveals. The per-token cross-entropy risk is hard to estimate because of a topological fact: among the possible states, finite risk and infinite risk each lie arbitrarily close to every instance of the other. Consequently no estimator---not merely the holdout average---is consistent at every state at which the risk is defined. Worse, inconsistent estimation persists under both bounding the expected sequence length and restricting to full-support models; and in that restricted setting the states at which inconsistency occurs are even dense. Two interesting ways out are identified, and neither is free. Way out 1: using a bounded context window, we can floor a model's next-token probabilities, making its risk finite exactly when the data-generating distribution has finite expected sequence length---a new, statistical rationale for a choice that was made on computational grounds, though the assumption it substitutes is itself beyond the reach of any test. Way out 2: …

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