While most cases of neonatal rashes are benign and self-limited, certain neonatal skin conditions require prompt diagnosis and targeted treatment to prevent severe morbidity and mortality. Recognition of high-risk neonatal rashes and early intervention can significantly improve patient outcomes. Categorizing the rash can help delineate a differential diagnosis and determine whether the presentation and physical examination have features of a high-risk rash. This issue offers a strategic approach to the evaluation of neonatal skin conditions and offers guidance for differentiating benign findings from those that should raise concern and lead to further evaluation and management.