The most critical component of a standing seam metal roof system—other than metal panel seams—is at vertical transitions and penetrations. Industry analysis has indicated that leaks in metal roof systems predominantly occur at metal panel joints and terminations. When specifying standing seam metal roof systems, the designer should be cognizant of details at terminations, penetrations, and flashings. The elimination of moisture entry can be achieved through the proper design of flashings at all vertical transitions and penetrations. This overview provides proper design requirements at the most common flashing points. Flashing design should be in compliance with the metal system manufacturers latest printed specifications.