Our study focuses on everyday manifestations of contemporary socioeconomic change. For a sample of young- and middle-aged German employees gathered in 2008 (N = 281), we investigate the relationship of perceived rising demands regarding (a) the labor market and (b) the workplace context with subjective job insecurity. Regression analyses reveal a positive effect of rising labor market demands on job insecurity, which is buffered by education. The effect of education on job insecurity is mediated by rising labor market demands. Rising workplace demands show no effect on job insecurity for West German employees. In contrast, East Germans who experience rising workplace demands report lower levels of job insecurity. Results are discussed with a particular focus on rising demands in employment relationships.