The City of Portland, Oregon is midway through the process of converting its street lighting system from the previous generation high-pressure sodium (HPS) to modern light-emitting diode (LED) technology. In getting to this point, the City purchased a large portion of its street lighting system and encountered a range of issues among the stakeholders, some of which were expected and some not. As these issues may be more or less common to other municipalities pursuing street lighting purchases and conversions, this paper identifies some of the challenges encountered and details of how they were addressed to help inform and facilitate future lighting transitions elsewhere. Preliminary discussion of the results and lessons learned are also included.