Standing at the crossroads of tax and employment law, the perennial problem of whether a worker is an employee or an independent contractor has been among the most important and common unemployment insurance tax issues. This problem is particularly complex in the trucking industry, due to the special conditions present in that industry’s working environment. In fact, it became so complicated that Minnesota legislators found it necessary to deal with it specifically in Minnesota Statute 268.035. In this article, I will rely on my own experience to explain the requirements of this legislation as it pertains to independent contractors in the trucking industry, and offer practical guidelines in certain common situations in that industry.