Plant disease phenotyping methodologies can vary considerably among testers and often suffer from shortcomings in their procedures and applications. This has been an important challenge in resistance breeding to brown rot, one of the most severe pre-and postharvest stone fruit diseases caused by Monilinia spp. Literature about methodologies for evaluating stone fruit susceptibility to brown rot is abundant but displays significant variations across the described approaches, limiting the ability to compare results from different studies. This is despite the fact that authors largely agree on the main factors influencing brown rot development, such as Monilinia inocula, environmental conditions, cultivars, fruit stage, and management practices. The present review first discusses ways to control or at least account for major factors affecting brown rot phenotyping studies. The second section describes in detail the different steps of fruit infection assays, comparing different protocols available in the literature with the objective of highlighting best practices and further improvement of phenotyping for brown rot susceptibility. Finally, experimental results from multi-year evaluation trials are also reported, highlighting year-to-year variability and exploring correlations of evaluation outcomes among years and assay types, suggesting that choice of phenotyping methodology must be carefully considered in breeding programs.