The dominant treatment paradigm for Paget-Schroetter syndrome has evolved to include immediate thrombolysis upon presentation with deep vein thrombosis (DVT), anticoagulation, and subsequent decompression of the thoracic outlet with first rib resection. Popularized by Machleder and Urschel in the 1980’s and 1990’s (Machleder HI. Evaluation of a new treatment strategy for Paget-Schroetter syndrome: spontaneous thrombosis of the axillary-subclavian vein. J Vasc Surg. 1993;17:305–15). They initially advocated an interval of anywhere from six weeks to three months between thrombolysis and surgery. More recently, a trend towards earlier surgical decompression has emerged in the literature, and timing of surgery after thrombolysis remains a debated topic in the management of this rare disease. Proponents of early decompression cite a lower interval reocclusion rate, improved long-term vein patency, shorter treatment duration, and earlier return to function as potential benefits, while delayed operation may reduce post-thrombotic local inflammation during dissection, can turn an emergent operation into an elective one, and may lead to equivalent functional outcomes. A subset of patients likely exists that are adequately treated with indefinite delay of surgery. Regardless of approach, outcomes tend to be good, underscoring the importance of good patient selection, avoiding unnecessary risk, and the need for ongoing standardized scholarship in this area.