<b><i>Background:</i></b> Mesh-related complications resulting from pelvic organ prolapse (POP) reconstruction operations may be a devastating experience leading to multiple and complex interventions. <b><i>Objectives:</i></b> The aim of the study was to describe the experience and time frame of management of mesh-related complications in women treated for POP or stress urinary incontinence in a tertiary center. <b><i>Methods:</i></b> 1,530 cases of mesh-related complications were accessed regarding their clinical presentation, number of surgeries, and timeline of surgical treatments to treat multiple clinical complaints until the ultimate operation where all the meshes were removed in a single tertiary center. <b><i>Results:</i></b> The studied population revealed to be a highly referred one with only 10.2% of the cases implanted at our center. Clinical presentation varied widely with 48.7% referring pain as the chief complaint, while 31.3% complained of voiding dysfunctions, 2.5% reported genital prolapses, 2.2% complained of vaginal problems, and 1.2% noted intestinal problems as the main clinical complaint. Only 4.8% of the cases presented mesh erosion at examination; 57.8% of the cases required more than 1 operation to address the mesh-related problems. Sixty-eight cases had more than 10 operations up to complete removal. Three clusters of patients could be identified: (i)–those from whom the mesh was promptly removed after clinical problems emerged, (ii) those with slowly evolving problems, and (iii) those with escalating problems despite treatment attempts. <b><i>Conclusions:</i></b> Mesh-related complications after pelvic floor reconstruction are an evolving disease with diverse clinical presentation. The identified time-related problems and the multiple failed attempts to treat their complications warrant attention with continuous monitoring of these patients and aggressive removal of the mesh if the clinical complaint cannot be swiftly managed.