A Measure-Theoretic Analysis of Reasoning: Structural Generalization and Approximation Limits

Recent work has shown that Transformers' compositional generalization is governed by \emph{complexity control}, initialization scale and weight decay, which steers training toward low-complexity reasoning solutions rather than high-complexity memorization. Existing analyses, however, treat complexity control as a single static hyperparameter choice, leaving open \emph{when} during training this control is actually decisive. We show that the memorization-versus-reasoning fate of a Transformer is determined within a sharp, identifiable window of training. On a controlled compositional task we find that (i)~weight decay applied for a single 25%-of-training window matches full-training weight decay in out-of-distribution (OOD) accuracy ($0.93$ vs $0.91$); (ii)~holding total regularization budget constant, placing it in the middle of training yields $5{-}9\times$ higher OOD accuracy than placing it early; (iii)~the boundary of the critical window is remarkably sharp, window onset shifted by as little as $100$ optimization steps causes mean OOD to jump from chance ($0.15$) to reasoning-regime ($0.61$); (iv)~the window's position depends systematically on initialization scale, but the basin of attraction for reasoning solutions \emph{shrinks} at small initialization, contradicting the prevailing recommendation that smaller initialization is uniformly better. We further show that the critical-window phenomenon is task-specific: it does not appear on grokking with modular arithmetic, where properly tuned constant weight decay matches scheduled weight decay.

Pre-trained transformers have demonstrated remarkable generalization abilities, at times extending beyond the scope of their training data. Yet, real-world deployments often face unexpected or adversarial data that diverges from training data distributions. Without explicit mechanisms for handling such shifts, model reliability and safety degrade, urging more disciplined study of out-of-distribution (OOD) settings for transformers. By systematic experiments, we present a mechanistic framework for delineating the precise contours of transformer model robustness. We find that OOD inputs, including subtle typos and jailbreak prompts, drive language models to operate on an increased number of fallacious concepts in their internals. We leverage this device to quantify and understand the degree of distributional shift in prompts, enabling a mechanistically grounded fine-tuning strategy to robustify LLMs. Expanding the very notion of OOD from input data to a model's private computational processes, a new transformer diagnostic at inference time is a critical step toward making AI systems safe for deployment across science, business, and government.

In this paper, we establish a collection of covering number bounds for linear function classes under various norm constraints on the inputs and matrices. We then combine these results with existing covering number bounds to derive improved estimates and, based on these estimates, develop generalization error bounds for single-layer Transformers. The resulting generalization bounds improve upon several existing results in the literature and, in particular, are independent of the input sequence length. Moreover, our generalization error bound decays at the rate $O(1/\sqrt{n})$, where $n$ denotes the sample size, thereby improving upon existing bounds that scale as $O((\log n)/\sqrt{n})$. Furthermore, our covering number analysis explicitly incorporates rank constraints on the underlying matrix classes, allowing us to characterize how low-rank structures affect the metric entropy and, consequently, the resulting generalization bounds for Transformer architectures.