Work Support Strategies (WSS) is a multiyear, multi-state initiative to implement reforms that help eligible low-income families get and keep a full package of work support benefits, including Medicaid, nutrition assistance (SNAP), and child care assistance. This report describes Kentucky's accomplishments and lessons learned during the initiative's first year. In this planning year, the state began building an infrastructure for data management and analysis, explored opportunities for policy alignment across key work supports, designed and tested business process changes in selected local offices, and began creating stronger relationships with external stakeholders.