The morphology of mitral valve (MV) prolapse and flail may be extremely variable, with dominant and secondary dynamic lesions. Any pathologic valve appears unique and different from any other. Three-dimensional (3D) transesophageal echocardiography is a powerful tool to evaluate the geometry, dynamics, and function of the MV apparatus and may be of enormous value in helping surgeons perform valve repair procedures. Indeed, in contrast to the surgical view, 3D transesophageal echocardiography can visualize MV prolapse and flail in motion and from different perspectives. The purpose of this special article is not to provide a comprehensive review of degenerative MV disease but rather to illustrate different types of mitral prolapse and flail as they appear from multiple 3D transesophageal echocardiographic perspectives using a series of clinical scenarios. Because in everyday practice, 3D transesophageal echocardiographic images of MV prolapse and flail are usually observed in motion, each scenario is accompanied by several videos. Finally, the authors provide for each scenario a brief description of the surgical techniques that are usually performed at their institution.