Purpose Stent migration remains the principal limitation of endovascular treatment for Nutcracker syndrome (NCS), with reported rates of 4.9–6.7%. We describe the early outcomes of a novel purely endovascular anchoring technique using an interlocking ovarian vein stent to augment left renal vein (LRV) stent fixation and reduce migration risk. Methodology A retrospective review was performed of the first five consecutive patients undergoing the ovarian vein anchoring technique for symptomatic NCS between 2024 and 2026. Following LRV stenting, a second stent was deployed from the ovarian vein through the interstices of the primary stent, creating an interlocking construct. Technical success was defined as successful deployment of the construct with restoration of unobstructed renal venous outflow. Primary outcomes were symptom improvement and primary stent patency. Results Five female patients underwent intervention. Median age was 39 years (range 33–56). All presented with chronic flank pain and pelvic symptoms refractory to conservative management. Technical success was achieved in all cases. There were no intraoperative complications, access-site complications, bleeding events, or perioperative thromboembolic events. Median length of stay was 3 days (range 2–5). Follow-up was available for four patients at a median of 3.75 months. Flank pain improved in all patients, pelvic symptoms improved in three, and two reported reduced analgesic requirements. Primary renal vein stent patency was 100% on ultrasound or CT, with no stent migration, thrombosis, reintervention, or loss of primary patency during follow-up. Conclusion The interlocking ovarian vein–LRV stent anchoring technique achieved 100% technical success, no stent migration, and sustained primary patency during early follow-up. By leveraging native venous anatomy to mechanically secure the renal vein stent, this endovascular approach may overcome the principal limitation of renal vein stenting for NCS.