Tokenization presents numerous challenges that significantly impact NLP system performance, particularly across languages and domains with different structural characteristics.

Language-Specific Issues: Languages without clear word boundaries (Chinese, Japanese, Thai) require specialized segmentation methods before or during tokenization. Morphologically rich languages (Finnish, Turkish, Hungarian) with extensive compounding and agglutination can generate extremely long words with complex internal structure that challenge typical tokenization approaches.

Domain-Specific Challenges: Technical vocabularies in fields like medicine, law, or computer science contain specialized terminology that may be inefficiently tokenized if not represented in training data. Social media text presents unique challenges with abbreviations, emojis, hashtags, and creative spelling that standard tokenizers struggle to handle appropriately.

Efficiency Tradeoffs: Larger vocabularies reduce token counts per text (improving efficiency) but increase model size and may worsen generalization to rare words. Smaller vocabularies produce longer token sequences but handle novel words better through compositional subword recombination.

Consistency Issues: Inconsistent tokenization between pre-training and fine-tuning or between model components can degrade performance. This becomes particularly challenging in multilingual settings where different languages may require different tokenization strategies.

Information Loss: Tokenization inevitably loses some information about the original text, such as whitespace patterns, capitalization details, or special characters that get normalized. These details can be significant for tasks like code generation or formatting-sensitive applications.

Modern NLP systems address these challenges through various strategies, including language-specific pre-tokenization, BPE dropout for robustness, vocabulary augmentation for domain adaptation, and byte-level approaches that can represent any Unicode character without explicit vocabulary limitations.