Reliable detection of bearing faults is essential for maintaining the safety and operational efficiency of rotating machinery. While recent advances in machine learning (ML), particularly deep learning, have shown strong performance in controlled settings, many studies fail to generalize to real-world applications due to methodological flaws, most notably data leakage. This paper investigates the issue of data leakage in vibration-based bearing fault diagnosis and its impact on model evaluation. We demonstrate that common dataset partitioning strategies, such as segment-wise and condition-wise splits, introduce spurious correlations that inflate performance metrics. To address this, we propose a rigorous, leakage-free evaluation methodology centered on bearing-wise data partitioning, ensuring no overlap between the physical components used for training and testing. Additionally, we reformulate the classification task as a multi-label problem, enabling the detection of co-occurring fault types and the use of prevalence-independent metrics based on the ROC curve. Beyond preventing leakage, we also examine the effect of dataset diversity on generalization, showing that the number of unique training bearings is a decisive factor for achieving robust performance. We evaluate our methodology on four widely adopted datasets: CWRU, Paderborn University (PU), University of Ottawa (UORED-VAFCLS) and HUST bearing. This study highlights the importance of leakage-aware evaluation protocols and provides practical guidelines for dataset partitioning, model selection, and validation, fostering the development of more trustworthy ML systems for industrial fault diagnosis applications.