Data management plans (DMPs) are an essential part of planning data-driven research projects and ensuring long-term access and use of research data and digital objects; however, as text-based documents, DMPs must be analyzed manually for conformance to funder requirements. This study presents a comparison of DMPs evaluations for 21 funded projects using 1) an automated means of analysis to identify elements that align with best practices in support of open research initiatives and 2) a manually-applied scorecard measuring these same elements. The automated analysis revealed that terms related to availability (90% of DMPs), metadata (86% of DMPs), and sharing (81% of DMPs) were reliably supplied. Manual analysis revealed 86% (n = 18) of funded DMPs were adequate, with strong discussions of data management personnel (average score: 2 out of 2), data sharing (average score 1.83 out of 2), and limitations to data sharing (average score: 1.65 out of 2). This study reveals that the automated approach to DMP assessment yields less granular yet similar results to manual assessments of the DMPs that are more efficiently produced. Additional observations and recommendations are also presented to make data management planning exercises and automated analysis even more useful going forward.