Recent initiatives have emphasized the potential role of Electronic Health Record (EHR) systems for improving tobacco use assessment and cessation. In support of these efforts, the goal of the present study was to examine tobacco use documentation in the EHR with an emphasis on free-text. Three coding schemes were developed and applied to analyze 525 tobacco use entries, including structured fields and a free-text comment field, from the social history module of an EHR system to characterize: (1) potential reasons for using free-text, (2) contents within the free-text, and (3) data quality issues. Free-text was most commonly used due to limitations for describing tobacco use amount (23.2%), frequency (26.9%), and start or quit dates (28.2%) as well as secondhand smoke exposure (17.9%) using a variety of words and phrases. The collective results provide insights for informing system enhancements, user training, natural language processing, and standards for tobacco use documentation.