Recovery has been generally found to replenish employees’ depleted resource reservoirs and benefit employees’ working state the next day (i.e., the “Battery-Recharging” effect). When the recovery period extends (e.g., weekends or holidays), and employees are thus able to replenish more resources, recovery’s positive effect, however, was found to be reversed to a negative Blue Monday syndrome describing employees’ psychological difficulties in switching back from a “recovery mode” to a “work mode”. Building upon conservation of resource and interdomain transition perspectives, we investigate the relationship between resource replenishment and psychological transition, and more importantly, how this relationship determines the valence of the extended recovery’s effects on work performance. In two multi-wave, multi-sourced field studies across different temporal settings of recovery, we found that gaining different types of recovery experiences (i.e., the major resource replenishment process of recovery) may improve or reduce the work reattachment process (i.e., the psychological transition from recovery to work), thereby exerting both positive and negative effects on employees’ post-recovery work performance. The length of recovery periods, efforts to mentally separate from the previous recovery mode, and social support at work were investigated as critical boundary conditions for these effects. We discussed how our study changes recovery research and management practice.