This paper develops the first end-to-end application of cross-sectional learning-to-rank to the S&P 500 weekly options (SPXW) zero-day-to-expiration surface, integrated with margin-aware position sizing, an abstention rule driven by model uncertainty, and a strict out-of-time integrity check. A LightGBM LambdaRank ranker scores a daily nine-strategy cross-section composed of eight delta-targeted short-put positions and a \textit{SKIP} candidate, trained against a path-aware Sortino-on-bars label computed at one-minute resolution. The framework is evaluated under index-option margin requirements, a tiered fee schedule, and bid-to-mid execution assumptions across a four-window walk-forward over 2021-2024 and a strictly held-out 2025 out-of-time slice. Seven sizing methods produce out-of-time annualized Sharpe ratios between 4.31 and 5.76, with the headline method reaching a Probabilistic Sharpe Ratio of 0.964 and a sample-period maximum drawdown of -2.28%, on a single hold-out year against a walk-forward range of 1.90 to 3.11. Out of time, every method exceeds three passive benchmarks (CBOE PUT, CBOE WPUT, SPX buy-and-hold) by at least 3.84 in Sharpe ratio and five internal selection baselines by at least 3.69. A two-by-two ablation of the confidence gate against the tail-risk features places 5.05 of the 5.59 out-of-time Sharpe gap over the CBOE PUT with the ranker and the selection layer, the two risk controls adding 0.54 between them. On walk-forward, where the gate binds, neither control comes close to the headline alone and their interaction supplies most of the result. A fifteen-group feature ablation shows that removing the multiplicative regime interactions collapses walk-forward statistical confidence.
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