Vision-language-action (VLA) models adapted through supervised fine-tuning (SFT) inherit a structural asymmetry: expert demonstrations teach the policy where success behavior lies, but provide no signal about where it ceases to be reliable. We argue that robust VLA adaptation should therefore be viewed not as further demonstration fitting, but as **Failure-Boundary Learning**---the problem of *Discovering*, *Localizing*, and *Shaping* the boundary between recoverable deviations and task failure. To instantiate this view, we propose **DLS**: built on a **real-grounded behavioral prior** from few real demonstrations and simulated co-training, DLS *discovers* failure boundaries at scale through on-policy digital twin rollouts. Rather than reducing each rollout to a binary label, **semantic progress localization** uses privileged simulator states to assign progress-aware signals that capture *where* the failure boundary is crossed, not merely *whether*. These signals drive **directional boundary shaping** in the flow dynamics---reinforcing success-producing denoising directions and suppressing failure-producing ones, without action likelihoods or auxiliary critics. Across real-robot manipulation tasks, DLS improves robustness over SFT and online RL baselines, especially under randomized initial states and unseen visual conditions.

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