This study investigates whether temporary contract volition and workers' expectations for contract renewal are boundary conditions to explain differences in temporary workers' job insecurity feelings and well-being. It is hypothesized that (1) low volition through higher job insecurity indirectly associates with lower well-being and that (2) temporary workers' expectations of contract renewal weakens the links between both low volition and high job insecurity and high job insecurity and impaired well-being. Results based on an international data set of 1755 temporary workers employed in the education, manufacturing, and service sectors supported the first hypothesis and partly also the second. More specifically, low preferences for temporary contracts associated via higher job insecurity with lower job satisfaction, impaired health, and higher irritation. Contract expectations placed a boundary condition upon this indirect relation; however, the negative association between high job insecurity and impaired well-being was not weakened but strengthened. In conclusion, particularly temporary workers with low contract volition and high job insecurity feelings, who have high expectations for contract renewal are at risk for impaired well-being. Hence, this study sheds light onto the question how volition for temporary work and expected contract renewal relate to job insecurity and associate with individual well-being.