The article addressed the impact of a transition to two flexible working time arrangements, employee- and employer-oriented, on subjective well-being (measured by job satisfaction and satisfaction with leisure time) from a longitudinal perspective. The study investigated which of three patterns of well-being, i.e., stability, recovery, or chronic strain / long-term improvement, are associated with these transitions. To address this question, the study used data from eleven waves (2003 – 2013) of the German Socio-Economic Panel. Fixed-effects analyses indicated that the well-being of individuals who switched to the employer-oriented flexible time arrangement followed a chronic strain pattern (women) or adaptation pattern (men). The effect of the transition to an employee-oriented flexible time arrangement is not unanimous: women appear to profit from this arrangement in the long run in terms of increased satisfaction with leisure time, whereas men experience deterioration in satisfaction with leisure time, followed by adaptation. At best, the effect of this transition on job satisfaction is short-lived for both genders.