Objective vs. Search: Decomposing What Makes a Good Tokeniser

Tokenisation is an integral part of the current NLP pipeline. Current tokenisation algorithms such as BPE and Unigram are greedy algorithms -- they make locally optimal decisions without considering the resulting vocabulary as a whole. We instead formulate tokeniser construction as a linear program and solve it using convex optimisation tools, yielding a new algorithm we call ConvexTok. We find ConvexTok consistently improves intrinsic tokenisation metrics and the bits-per-byte (BpB) achieved by language models; it also improves downstream task performance, but less consistently. Furthermore, ConvexTok allows the user to certify how far their tokeniser is from optimal, with respect to a certain objective, via a lower bound, and we empirically find it to be within 1% of optimal at common vocabulary sizes.

The Unigram tokenizer uses an elegant representation which makes it straightforward to edit vocabularies, but its training is comparatively heavy and complex. We introduce MinGram (Minimalist Unigram), which keeps the token-list representation but simplifies training using a BPE-derived seed vocabulary, Hard EM on a minimum-token path, and a single flat score-pruning step. This removes the suffix array, the forward-backward pass, and the iterative prune loop, leaving a procedure that requires little beyond tokenizer inference itself. By making token count the primary objective and using a Unigram score only as a tiebreak, MinGram keeps the compression of pure token-count methods while retaining much of the morphological alignment and downstream quality of probabilistic ones. Across six languages, MinGram compresses better than both BPE and standard Unigram, and a compression-oriented variant matches the strongest token-count compressors while retaining substantially higher morphological alignment. In controlled downstream language-model training, Unigram-family tokenizers, with MinGram among the best, consistently beat BPE in bits-per-byte.

Language model tokenizers are typically selected with minimal evaluation, despite the fact that their design choices directly impact model capabilities. This can be partly attributed to a limited understanding of which tokenizer properties affect which aspects of downstream performance. We introduce TokEval, a framework of tokenizer evaluation metrics that goes beyond standard measures like fertility and compression rate to capture linguistically and structurally meaningful properties, e.g., UTF-8 character boundary integrity and digit place-value boundary alignment for mathematics. To validate whether these metrics are predictive of downstream model performance, we conduct controlled language model pretraining experiments, varying solely the tokenizers' training data mixture, pretokenization strategy, and training algorithm. We evaluate the resulting models on bits-per-byte (a tokenizer-agnostic version of perplexity) and several benchmarks, spanning linguistic understanding, mathematical reasoning, and code generation. Our experiments suggest that different intrinsic properties have different impacts on model abilities: information-theoretic metrics predict language modeling abilities (Spearman rho up to 0.80), while structure-sensitive metrics, such as those measuring digit and line-break handling, correlate with task accuracy. We hope TokEval enables more principled tokenizer evaluation, replacing pretraining sweeps with intrinsic measurement wherever the two agree.