May-Thurner syndrome is a unique condition that strikes mainly young people. Its prevalence is likely underestimated and perhaps ranges from 22 to 32%. May-Thurner is under reported and often miss-diagnosed in accident and emergency, which can result in long term complication (post thrombotic syndrome) with its detrimental effect in this young age group. We describe a case of May-Thurner syndrome, a near miss, with review of published treatment and follow up strategies. This includes direct catheter thrombolysis, angioplasty, stenting, and IVC filter placement. Our patient has made a good recovery on follow up.