When Does Online Imitation Learning Help in LLM Post-Training? The Role of (Non-)Realizability Beyond Horizon

Online imitation learning (IL), particularly on-policy distillation, has emerged as a strong LLM post-training approach, often outperforming offline supervised fine-tuning (SFT). Yet a principled understanding of when and why online helps remains unclear. In this work, we challenge the view that error accumulation is the main source of online IL's advantage, and instead show that the benefits of online interaction depend critically on whether the setting is realizable, i.e., whether the student policy class can represent the expert policy. Under realizability, we empirically find that offline IL already matches expert performance. In contrast, in non-realizable (misspecified) settings, we prove that offline IL encounters an information-theoretic bottleneck even when horizon $H=1$, and propose a structural characterization of misspecification relative to the reward, under which online IL provably achieves high performance despite large expert-student discrepancy.