Recent Vision-Language-Action (VLA) models show strong generalization capabilities, yet they lack introspective mechanisms for anticipating failures and requesting help from a human supervisor. We present \textbf{INSIGHT}, a learning framework for leveraging token-level uncertainty signals to predict when a VLA should request help. Using $π_0$-FAST as the underlying model, we extract per-token \emph{entropy}, \emph{log-probability}, and Dirichlet-based estimates of \emph{aleatoric and epistemic uncertainty}, and train compact transformer classifiers to map these sequences to help triggers. We explore supervision regimes for strong or weak supervision, and extensively compare them across in-distribution and out-of-distribution tasks. Our results show a trade-off: strong labels enable models to capture fine-grained uncertainty dynamics for reliable help detection, while weak labels, though noisier, still support competitive introspection when training and evaluation are aligned, offering a scalable path when dense annotation is impractical. Crucially, we find that modeling the temporal evolution of token-level uncertainty signals with transformers provides far greater predictive power than static sequence-level scores. This study provides the first systematic evaluation of uncertainty-based introspection in VLAs, opening future avenues for active learning and for real-time error mitigation through selective human intervention.