We study the problem of entropy calibration, which asks whether a language model's entropy over generations matches its log loss on human text. Past work found that models are miscalibrated, with entropy per step increasing as generations grow longer, due to error accumulation. To calibrate the model and improve text quality, it has become standard practice to truncate the distribution, but this approach reduces output diversity, which we would like to avoid. Therefore, in this paper, we ask: does miscalibration improve automatically with scale, and if not, is it theoretically possible to calibrate without tradeoffs? To build intuition, we first study a simplified theoretical setting to characterize the scaling behavior of miscalibration with respect to dataset size. We find that the rate of scaling depends on the power law exponent of the data distribution -- in particular, for a power law exponent close to 1, the scaling exponent is close to 0, meaning that miscalibration improves very slowly with scale.

Deep neural networks (DNNs) are the de facto methodology in many artificial intelligence areas nowadays [25, 37]. How to effectively train a deep network has been a central topic for decades.

Named Entity Recognition (NER) serves as a foundational component in many natural language processing (NLP) pipelines. However, current NER models typically output a single predicted label sequence without any accompanying measure of uncertainty, leaving downstream applications vulnerable to cascading errors. In this paper, we introduce a general framework for adapting sequence-labeling-based NER models to produce uncertainty-aware prediction sets. These prediction sets are collections of full-sentence labelings that are guaranteed to contain the correct labeling with a user-specified confidence level. This approach serves a role analogous to confidence intervals in classical statistics by providing formal guarantees about the reliability of model predictions. Our method builds on conformal prediction, which offers finite-sample coverage guarantees under minimal assumptions. We design efficient nonconformity scoring functions to construct efficient, well-calibrated prediction sets that support both unconditional and class-conditional coverage. This framework accounts for heterogeneity across sentence length, language, entity type, and number of entities within a sentence. Empirical experiments on four NER models across three benchmark datasets demonstrate the broad applicability, validity, and efficiency of the proposed methods.

It is widely recognized that reinforcement learning (RL) fine-tuning of large language models often leads to diversity collapse, where outputs lack variety. Prior work has proposed a range of heuristics to counteract this effect, but these methods are ad hoc: they frequently trade off correctness for diversity, their effectiveness varies across tasks, and in some cases they even contradict one another. In this work, we place these observations on a rigorous foundation. We first provide a formal proof of why RL fine-tuning exhibits diversity collapse via a selection and reinforcement bias. Next, we make a key observation that any reward modification to address diversity collapse only needs to be applied on the correct trajectories. Building directly on this analysis, we introduce a principled method -- differential smoothing -- that provably improves both correctness and diversity, outperforming vanilla RL as well as widely used entropy-based heuristics. Our theory precisely characterizes when existing heuristics help and why they fail, while showing that differential smoothing is universally superior. Extensive experiments with models from 1B to 7B parameters, across domains including CountDown and real-world mathematical reasoning, demonstrate consistent gains. Differential smoothing improves both Pass@1 and Pass@k, with up to 6.7% improvements on AIME24 dataset.

We study the problem of entropy calibration, which asks whether a language model's entropy over generations matches its log loss on human text. Past work found that models are miscalibrated, with entropy per step increasing (and text quality decreasing) as generations grow longer. This error accumulation is a fundamental problem in autoregressive models, and the standard solution is to truncate the distribution, which improves text quality at the cost of diversity. In this paper, we ask: is miscalibration likely to improve with scale, and is it theoretically possible to calibrate without tradeoffs? To build intuition, we first study a simplified theoretical setting to characterize the scaling behavior of miscalibration with respect to dataset size. We find that the scaling behavior depends on the power law exponent of the data distribution -- in particular, for a power law exponent close to 1, the scaling exponent is close to 0, meaning that miscalibration improves very slowly with scale. Next, we measure miscalibration empirically in language models ranging from 0.5B to 70B parameters. We find that the observed scaling behavior is similar to what is predicted by the simplified setting: our fitted scaling exponents for text are close to 0, meaning that larger models accumulate error at a similar rate as smaller ones. This scaling (or, lack thereof) provides one explanation for why we sample from larger models with similar amounts of truncation as smaller models, even though the larger models are of higher quality. However, truncation is not a satisfying solution because it comes at the cost of increased log loss. In theory, is it even possible to reduce entropy while preserving log loss? We prove that it is possible, if we assume access to a black box which can fit models to predict the future entropy of text.

D.2 Additional experiment results Comparison across related baselines.