The interest in flexible job search behaviour (FJSB) among unemployed jobseekers, i.e., the extent to which jobseekers also look for jobs that deviate from their studies and earlier work experience, has grown considerably in recent years. Yet, there is large disagreement on both its consequences and drivers. Career scholars as well as policymakers believe that FJSB is important for unemployed and can improve their employment prospects. However, evidence from human resource (HR) literature raises doubts whether FJSB can enhance re-employment success. Similarly, whereas the career literature links FJSB to positive attitudes, such as career adaptability, the HR literature suggests that people searching flexibly may feel pushed into this behaviour due to more negative reasons, like few labour market perspectives. The aim of this study is examining these opposing expectations. We focus on three FJSB types: flexibility with respect to pay/hierarchical level, skill use and commuting time. Hypotheses are tested using two-wave data with 672 unemployed. Results indicate, among others, that career-adaptable people are not inclined to search more flexibly. In addition, FJSB may in certain cases hamper people's re-employment likelihood. People searching more flexibly also more often became underemployed and as such experienced a more negative job quality.