The NOAA Office of Coast Survey (OCS) embarked on a journey to completely overhaul their Hydrographic Surveys Specifications and Deliverables (HSSD) to better suit the rapidly evolving hydrographic industry. In conjunction with teams of subject-matter experts assembled to compose the new specifications, OCS took a unique approach to development by involving both programmers and field units during the writing phase, to ensure the specifications could be readily converted into automated tools to test compliance, and could be easily implemented into an operational setting. Working together with the Center for Coastal and Ocean Mapping/Joint Hydrographic Center (CCOM/JHC) and the NOAA Hydrographic Systems and Technology Branch (HSTB), the teams proactively developed quality analysis and processing tools (e.g., HydrOffice QC Tools, and NOAA Pydro applications) which provided a feedback loop of improvements to the specifications. Initial assumptions in the writing process were tested in-office using archived data before releasing a draft copy of the specifications for beta field testing. Training materials and lines of rapid communication were established with field units to aid in the beta testing of the draft specifications and to ensure efficient feedback to the writing teams. This paper discusses the iterative implementation and testing that occurred while re-envisioning the HSSD. From the proactive development of tools, to challenging of initial assumptions with in-office testing, to the NOAA field unit operational beta-testing of draft specifications, this paper will discuss how each of these activities shaped the final product. Finally, this paper also delves into future software and specification developments, aiming to enhance the overall efficiency and compatibility of the HSSD framework.