When considering the acquisition of a motor carrier operation, a number of due diligence matters specific to transportation should be analyzed, including licensure, permitting and an analysis of federal or state regulatory regimes applicable to the motor carrier. If the target carrier utilizes an independent contractor work-force, understanding and assessing those relationships within the unique transportation fact-pattern are critical. The assessment for regulatory compliance of the independent contractor agreement and for areas of exposure given state law precedent and statutory exemptions based on contractor domiciles are both key to structuring a proper merger or acquisition. Equally important is consideration of post-acquisition restructuring when certain exposures have been identified during the due diligence process. The transaction often occurs in a rapidly changing legal environment where sensitivity to proposed legislative changes and recent common law precedent impacting transportation operations may be pivotal to an investment decision.