Structured entry and reporting in medicine remains an elusive goal. Poor adoption of clinical structured entry for documentation results in part from the inherent complexity of entering patient histories, which are generally unstructured. The authors have developed a structured entry tool that has been adopted by practicing physicians for documentation of clinical encounters. To evaluate the impact of this tool on clinical documentation, the authors have performed two comparative studies investigating note complexity. Authors compared documents generated with a standard dictation/transcription model with documents generated with structured entry. Overall, documents generated with the structured entry and reporting tool contained 64% more concepts (P<0.01) than dictated documents while maintaining the same complexity. Depth and complexity of documentation with the structured entry and reporting tool varied by clinician user and by note sub-section.