A 33-year-old female presented to the emergency department of our hospital with urosepsis and hematuria with clot retention secondary to a complicated pyelolithotomy for left-sided pelvic calculus. A percutaneous nephrostomy was placed for drainage as a DJ stent could not be traversed into the left renal pelvis with retrograde pyelography demonstrating complete cut-off at L4–L5 level. After stabilization, she was found to have uretero-pelvic junction obstruction (UPJO) in left solitary functioning kidney with long-segment upper ureteric stricture and nadir serum creatinine 1.5 mg/dL. Nephrostogram and CT scan revealed an intra-renal pelvis with no passage of contrast into the ureter. Primary hyperparathyroidism secondary to parathyroid adenoma was also detected and she underwent excision of the same. The long-segment ureteric stricture and need for a wide drainage ruled out pyeloplasty and ureterocalicostomy as treatment options. A wide-bore communication between the lower calyx and bladder was necessary and robot assisted ileocalicostomy was performed in this case. A 20-cm-long segment of ileum was used to replace the ureter with a suprapubic 16 Fr Foley’s catheter as splint. Postoperative course was uneventful with all tubes removed by third postoperative week. Nephrostogram demonstrated gravity-dependent drainage into the bladder with no leak or anastomotic narrowing. The patient is doing well at 6 months of follow-up with a stable renal function. Robot assisted ileocalicostomy is a safe and effective technique which provides wide gravity-dependent drainage in complex UPJO with long-segment ureteric stricture and intra-renal pelvis.