Chronic prostatitis/chronic pelvic pain syndrome (CP/CPPS) is defined as chronic pain or discomfort in the pelvic region for at least 3 of the past 6 months. It is variably associated with lower urinary tract symptoms, psychosocial consequences, and sexual dysfunction. Specific test systems or biomarkers for a definitive diagnosis are still not available. The purposes of the basic diagnostic assessment are to determine the individual spectrum of symptoms and to rule out differential diagnoses of pelvic pain. Patient-reported outcome measures (PROMs) like the National Institutes of Health Chronic Prostatitis Symptom Index (NIH-CPSI) are valuable instruments for the initial diagnostic assessment and to evaluate treatment response. Classification systems like UPOINTS (urinary, psychosocial, organ specific, infection, neurologic/systemic, tenderness of skeletal muscles, sexual dysfunction) are valuable tools to determine the individual spectrum of symptoms, to guide the adapted diagnostic assessment, and to identify relevant targets for a multimodal and tailored treatment. Close urological monitoring of CP/CPPS patients is usually necessary, especially to minimize the unwarranted use of antibiotics in the case of undulating complaints.