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BACKGROUND: A 'watering can penis' secondary to penile tuberculosis is an extremely rare clinical entity. Retrograde Urethrography - Voiding Cystourethrography evaluation of the urethra and the urinary bladder plays a very important role in the diagnostics as well as further management of the urethral abnormalities. To the best of our knowledge, this is only the second case in literature where a ‘watering can penis’ was noted secondary to penile TB. This is also the first documented case of ‘watering can penis’ as a consequence of venereal transmission of TB. CASE REPORT: A 50-year-old male presented with multiple discharging sinuses along the penis. RGU revealed multiple, contrast-filled, narrow, irregular, fistulous tracts arising from the pendulous part of the anterior urethra. This distal segment of the pendulous part of the anterior urethra also showed significant distortion and irregular, beaded narrowing. VCUG showed a markedly-contracted and small-capacity urinary bladder with a thickened, irregular and edematous wall with multiple hypertrophied trabeculae along its walls. The patient was administered anti-tubercular treatment. At the end of this treatment regimen, a repeat RGU-VCUG will be performed and decision regarding urethroplasty and further management will be planned depending upon the presence of any remaining fistulas or strictures involving the urethra. CONCLUSIONS: 'Watering can penis' as a result of penile TB is a very rare clinical entity. The differential diagnoses of a 'watering can penis' should be kept in mind in the evaluation of these patients. RGU and VCUG evaluation is an important conventional imaging modality used in the evaluation of urethral strictures and fistulas in case of 'watering can penis'.