In this paper, we present Machine Learning (ML) solutions to address the reliability challenges likely to be encountered in advanced wireless systems (5G, 6G, and indeed beyond). Specifically, we introduce a novel loss function to minimize the outage probability of an ML-based resource allocation system. A single-user multi-resource greedy allocation strategy constitutes our application scenario, for which an ML binary classification predictor assists in selecting a resource satisfying the established outage criterium. While other resource allocation policies may be suitable, they are not the focus of our study. Instead, our primary emphasis is on theoretically developing this loss function and leveraging it to train an ML model to address the outage probability challenge. With no access to future channel state information, this predictor foresees each resource's likely future outage status. When the predictor encounters a resource it believes will be satisfactory, it allocates it to the user. The predictor aims to ensure that a user avoids resources likely to undergo an outage. Our main result establishes exact and asymptotic expressions for this system's outage probability. These expressions reveal that focusing solely on the optimization of the per-resource outage probability conditioned on the ML predictor recommending resource allocation (a strategy that -at face value -looks to be the most appropriate) may produce inadequate predictors that reject every resource. They also reveal that focusing on standard metrics, like precision, false-positive rate, or recall, may not produce optimal predictors. With our result, we formulate a theoretically optimal, differentiable loss function to train our predictor. We then compare predictors trained using this and traditional loss functions namely, binary cross-entropy (BCE), mean squared error (MSE), and mean absolute error (MAE). In all scenarios, predictors trained using our novel loss function provide superior outage probability performance. Moreover, in some cases, our loss function outperforms predictors trained with BCE, MAE, and MSE by multiple orders of magnitude. Additionally, when applied to another ML-based resource allocation scheme (a modified greedy algorithm), our proposed loss function maintains its efficacy.