This article explores the relationships of job insecurity and regional unemployment rate with job attitudes and work-related strain. The authors considered the personality attribute flexibility as a potential moderator. Their results revealed job insecurity to be negatively associated with job involvement and career satisfaction and positively with readiness to make concessions and strain. Moreover, with an increasing level of subjective (qualitative) job insecurity, individuals low in flexibility reported lower career satisfaction. In contrast, where objective job insecurity (unemployment rate) was high, these low flexibility participants showed higher career satisfaction. They were also more ready to make concessions and more involved with their job than those high in flexibility. Finally, the study found the proposed buffering effect, as those high in flexibility experienced less health impairment when perceived (quantitative) job insecurity and regional unemployment rate were high. Strategies of coping with uncertainty as well as options regarding strengthening flexibility are discussed.