Over the past five years or so, private equity firms and a steady stream of strategic buyers in the trucking market have taken a renewed and active interest in acquiring transportation businesses.  Despite an active market, in part due to greater availability of loans and underwriting insurance, deal failures have occurred with greater frequency. In large part, the failures pivot on technical legal issues involved in transportation-related transactions. Such issues include permits, authorities, and licensing problems often in highly sensitive areas involving hazmat, TSA, and federal maritime commission regulations. A fundamental misunderstanding of independent contractor documentation and operational practices also lead to problems. In addition, the asset-light logistics laws (where penalties have been added to inspire greater enforcement) have given insurers significant pause, while also discouraging sellers who are called upon to place greater sums in escrow. A number of these issues can be discovered and resolved via a mock due diligence audit. With some foresight by current owners as to the future sale of the transportation business, a mock audit might benefit both buyers and sellers—long before a deal is being discussed.