On-Policy Distillation (OPD) trains a student on its own generations using teacher feedback. With different tokenizers, comparing teacher and student predictions requires alignment at both sequence and vocabulary levels. In this paper, we examine whether expanding this alignment coverage improves learning. Across three heterogeneous teacher--student pairs on mathematical reasoning and code generation, strict 1:1 groups already cover most student-generated tokens despite substantial vocabulary mismatch. On responses sampled from the students before distillation, the shared vocabulary retains nearly all teacher and student probability mass at strictly aligned positions on average. Restricting reverse KL to a student-selected top-16 subset of the shared vocabulary at each strict position achieves accuracy comparable to full shared-vocabulary OPD, outperforming the evaluated cross-tokenizer baselines. Adding mean squared error supervision on span log-probabilities in mismatch groups gives complete supervision coverage, yet reduces accuracy. At checkpoints from training with only the strict loss, the span gradients show weak or negative directional agreement with the strict gradients and grow in magnitude relative to them. These diagnostics may help explain the accuracy drop from adding span supervision. Our findings motivate a shift from maximizing alignment coverage to prioritizing supervision reliability: compact supervision at strict positions can be more effective than broader coverage that introduces weakly aligned or conflicting training signals.

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