The Communication Bottleneck: A Round-Trip Study of Compositional Serialization in Language Models

When language models reason in chain-of-thought or collaborate in pipelines, they serialize structured information into natural language. How much compositional structure survives this bottleneck? We propose a round-trip protocol that answers this question empirically for tree-structured symbolic expressions. A generator converts a procedurally generated arithmetic expression into a word problem, a separate extractor recovers the expression from the word problem alone, and symbolic equivalence provides an exact oracle. Evaluating all pairwise combinations of fifteen models yields a communication matrix whose marginals separate generation quality from extraction quality. Three main findings emerge. First, the channel is lossy and asymmetric: swapping which model generates and which extracts shifts accuracy by up to 53.2 points, and the best pair reaches 82.0\% by combining different models on each end rather than the same model on both. Second, at least 84\% of round-trip failures originate at generation, and difficulty is driven by tree structure (operator count, depth, right-branching) rather than model family. Third, the channel is trainable: $\sim3600$ fine-tuning examples that share the evaluation's operators and tree shapes lift every open-weight model above untrained GPT-5, an upper bound under matched semantics. A disjoint-domain regime with new operators and vocabulary also raises every open-weight model, confirming the gain is not an artifact of matched semantics, though a gap to the frontier remains. Together these results identify compositional serialization as a primary limiting factor when models communicate hierarchical structure through natural language.