Introduction: Vascular compression of ureter by aberrant lower polar vessels, retrocaval compression and ovarian vein has been described in the past. Still rarer is the ureteric obstruction with the crossing of testicular vein. We present a case of Bilateral testicular vein syndrome masquerading as Ureteropelvic junction obstruction(UPJO), its intra-operative diagnosis and management. Methods: Index patient is a 18-year-old male, presented with history of bilateral flank pain since 7 months, colicky in nature, requiring intravenous analgesics. There was no significantly contributing past history. He was evaluated elsewhere with abdominal ultrasonography which was suggestive of bilateral gross hydronephrosis. Non-contrast computed tomography(NCCT), done during an acute episode revealed bilateral gross hydronephrosis with probable site of obstruction at UPJ. Diuretic renography in the form of DTPA Scan consolidated the findings of NCCT revealing bilateral compromised cortical function and obstruction to outflow at UPJ. With the given history and evaluation, patient was diagnosed to have Bilateral UPJO and planned for bilateral robot-assisted pyeloplasty. Intraoperatively, on the left side, at pyelotomy the ureter seemed dilated across UPJ raising questions over pre-operative diagnosis. Consequently distal patency check was undertaken to confirm the site of obstruction. After gentle distal ureteric dissection, extrinsic compression at the site of crossing left testicular vein was found to be the site of actual ureteric obstruction. To relieve this compression, the ureter was super positioned over a posteriorized gonadal vein with a subsequently successful distal patency check. Taking lessons from the left side, we started with distal ureteric dissection and surprisingly found extrinsic compression with right testicular vein on the right side as well. Site of compression was visualised as fibrosed ureteric segment which was excised and ureteroureterostomy was done super positioned over a posteriorized right gonadal vein. Results: The patient had an uneventful post-operative course and bilateral double-J stents were removed at 3 weeks. Follow-up renogram at 3 months documented the resolving bilateral hydronephrosis and unobstructed drainage. Conclusions: Lessons learned from the given case are- Contrast-enhanced CT imaging could have suggested ureteric compression with gonadal vein pre-operatively, Distal patency check is vital when there is dilatation across PUJ, When in doubt, distal ureteric dissection is a better approach and preservation of ureteric vascularity is of paramount importance SOURCE OF Funding: None