# Best-of-Tails: Bridging Optimism and Pessimism in Inference-Time Alignment

arXiv: https://arxiv.org/abs/2603.06797 · HTML: https://mlsanity.com/paper/2603.06797/

## Key facts

- Cited by 3 papers in the map (data through 14 Oct 2026).
- Placed in LLM preference optimization methods, one of 10 directions in LLM alignment / RLHF / preference optimisation.
- Builds on 55 of its 64 references that are in the map.
- First posted on arXiv 6 Mar 2026.

## Placed in

- LLM alignment / RLHF / preference optimisation / [LLM preference optimization methods](https://mlsanity.com/alignment/llm-preference-optimization-methods/)

## Builds on (most cited first, 30 of 55)

- [Proximal Policy Optimization Algorithms](https://mlsanity.com/paper/1707.06347/) (2017)
- [The Llama 3 Herd of Models](https://mlsanity.com/paper/2407.21783/) (2024)
- [Chain-of-Thought Prompting Elicits Reasoning in Large Language Models](https://mlsanity.com/paper/2201.11903/) (2022)
- [Training Verifiers to Solve Math Word Problems](https://mlsanity.com/paper/2110.14168/) (2021)
- [Direct Preference Optimization: Your Language Model is Secretly a Reward Model](https://mlsanity.com/paper/2305.18290/) (2023)
- [Measuring Massive Multitask Language Understanding](https://mlsanity.com/paper/2009.03300/) (2020)
- [Scaling Laws for Neural Language Models](https://mlsanity.com/paper/2001.08361/) (2020)
- [Measuring Mathematical Problem Solving With the MATH Dataset](https://mlsanity.com/paper/2103.03874/) (2021)
- [Deep reinforcement learning from human preferences](https://mlsanity.com/paper/1706.03741/) (2017)
- [Tree of Thoughts: Deliberate Problem Solving with Large Language Models](https://mlsanity.com/paper/2305.10601/) (2023)
- [Mistral 7B](https://mlsanity.com/paper/2310.06825/) (2023)
- [Learning to summarize from human feedback](https://mlsanity.com/paper/2009.01325/) (2020)
- [Gemma 2: Improving Open Language Models at a Practical Size](https://mlsanity.com/paper/2408.00118/) (2024)
- [Scaling LLM Test-Time Compute Optimally can be More Effective than Scaling Model Parameters](https://mlsanity.com/paper/2408.03314/) (2024)
- [Self-RAG: Learning to Retrieve, Generate, and Critique through Self-Reflection](https://mlsanity.com/paper/2310.11511/) (2023)
- [Pythia: A Suite for Analyzing Large Language Models Across Training and Scaling](https://mlsanity.com/paper/2304.01373/) (2023)
- [Fast Inference from Transformers via Speculative Decoding](https://mlsanity.com/paper/2211.17192/) (2022)
- [Scaling Laws for Reward Model Overoptimization](https://mlsanity.com/paper/2210.10760/) (2022)
- [Large Language Monkeys: Scaling Inference Compute with Repeated Sampling](https://mlsanity.com/paper/2407.21787/) (2024)
- [AlpacaFarm: A Simulation Framework for Methods that Learn from Human Feedback](https://mlsanity.com/paper/2305.14387/) (2023)
- [OpenAssistant Conversations -- Democratizing Large Language Model Alignment](https://mlsanity.com/paper/2304.07327/) (2023)
- [RAFT: Reward rAnked FineTuning for Generative Foundation Model Alignment](https://mlsanity.com/paper/2304.06767/) (2023)
- [Interpretable Preferences via Multi-Objective Reward Modeling and Mixture-of-Experts](https://mlsanity.com/paper/2406.12845/) (2024)
- [ReST-MCTS*: LLM Self-Training via Process Reward Guided Tree Search](https://mlsanity.com/paper/2406.03816/) (2024)
- [Statistical Rejection Sampling Improves Preference Optimization](https://mlsanity.com/paper/2309.06657/) (2023)
- [Towards Revealing the Mystery behind Chain of Thought: A Theoretical Perspective](https://mlsanity.com/paper/2305.15408/) (2023)
- [The Unlocking Spell on Base LLMs: Rethinking Alignment via In-Context Learning](https://mlsanity.com/paper/2312.01552/) (2023)
- [Reward Model Ensembles Help Mitigate Overoptimization](https://mlsanity.com/paper/2310.02743/) (2023)
- [Meta-Rewarding Language Models: Self-Improving Alignment with LLM-as-a-Meta-Judge](https://mlsanity.com/paper/2407.19594/) (2024)
- [Regularizing Hidden States Enables Learning Generalizable Reward Model for LLMs](https://mlsanity.com/paper/2406.10216/) (2024)

## Built on by (most cited first, 3 of 3)

- [Best-of-Evidence: Best-of-N Selection under Partial Verification](https://mlsanity.com/paper/2607.20950/) (2026)
- [ExpBoN: Exponential-Noise Best-of-n for Efficient Test-Time LLM Alignment](https://mlsanity.com/paper/2609.21899/) (2026)
- [Tail Competition Explains Scaling in Best-of-N Sampling for Verifiable Problems](https://mlsanity.com/paper/2610.19362/) (2026)

## Abstract (arXiv)

Inference-time alignment effectively steers large language models (LLMs) by generating multiple candidates from a reference model and selecting among them with an imperfect reward model. However, current strategies face a fundamental dilemma: ``optimistic'' approaches like Best-of-N suffer from reward hacking, while ``pessimistic'' regularized methods often stifle the exploration needed to discover high-quality responses. In this work, we formalize this trade-off through the lens of regret minimization, demonstrating that the optimal strategy depends critically on the tail behavior of the reward distribution. We show theoretically that light-tailed regimes favor optimism to unearth high-quality outliers, whereas heavy-tailed regimes require pessimism to guard against reward mis-calibration in the extremes. Guided by this insight, we introduce Best-of-Tails (BoT), an adaptive inference-time alignment framework that uses Tsallis divergence as a tunable regularizer to provide a finer granularity of interpolation between these extremes. BoT uses the Hill estimator to characterize reward-tail heaviness on a per-prompt basis and dynamically adjusts its selection rule to balance exploration gains against alignment error. Across math, multiple-choice reasoning, and human-preference evaluations, BoT improves alignment performance across a range of reference and reward model configurations relative to fixed-strategy baselines.