This paper empirically examines factors affecting older workers' Entered Employment Rate using panel data models and identifies relevant policy implications. It starts with the background of an aging workforce and the current economic recession that makes training older workers critical. After reviewing literature on older workers' attributes and the uniqueness of older worker training, the paper tests two hypotheses: (1) some Workforce Investment Act (WIA) training and related service combinations can be identified to inform strategic decision-making about future allocations of WIA funds to serve older workers; and (2) WIA program success with older workers is sensitive to cyclical changes in labor market conditions. The paper relies on Workforce Investment Act Standardized Record Data 2007 data and Bureau of Labor Statistics unemployment data. After descriptive statistics, this paper adopts panel data models and empirically examines the impacts of unemployment rates and various WIA services and training on older workers' Entered Employment Rate. Older dislocated workers and older adults are examined separately. An innovative two-sector unemployment rate measure is adopted. Older workers' demographic and socioeconomic conditions are controlled and examined in the empirical investigation. Test findings as well as data attributes are discussed. This paper concludes with policy implications.