Organizations benefit from older workers' contributions even past the threshold of retirement, yet little is known about what motivates older workers to pursue bridge employment in their current organizations. Perceived organizational support (POS) typically helps organizations retain employees, yet some older workers may ironically be repelled by POS to the extent that it imposes an undesirable, excessive obligation. In this paper, we develop and test a model of how older workers' intentions to engage in bridge employment towards their current organization are contingent upon the interaction between two central elements of older workers' employment relationships: (1) perceived organizational support (POS), and (2) the type of psychological contract they endorse. In Study 1, using data from two samples (Study 1a N = 168; Study 1b time-lagged N = 157), we found that POS increased bridge employment intentions to the current organization among older workers endorsing a relational psychological contract. However, we also found that POS decreased bridge employment intentions to the current organization among older workers endorsing a transactional psychological contract. In Study 2 (N = 348), we unpacked the underlying mechanisms (role expansion and excessive obligation to the organization) that explain the interaction effects. The results indicate that how POS ‘fits’ with older workers' psychological contracts informs their motivation to engage in bridge employment.