Work time control may offer opportunities, but also implies risks for employee recovery, influenced by increased work-related ICT use and overtime work. However, this risk–opportunity tradeoff remains understudied. This study aimed to test two different models of associations between work time control, work-related ICT use, overtime work, and the need for recovery. These models were constructed based on data on office workers with flexible work arrangements. Cross-sectional data were obtained with questionnaires (n = 2582) from employees in a Swedish multi-site organization. Regression models treated the three determinants of the need for recovery either as independent, or as linked in a causal sequence. The test of independent determinants confirmed that more work time control was associated with less need for recovery, whereas more ICT use and overtime work were associated with a higher need for recovery. In a test of serial mediation, more work time control contributed to a greater need for recovery through more ICT use and then more overtime work. Work time control also had a competitive, indirect effect through a negative association with overtime work. Our results suggest that work time control is beneficial for employee recovery, but may for some be associated with more work-related ICT use after regular working hours, thus increasing recovery needs. Policies that support work time control can promote recovery, but employers must attend to the risk of excessive use of ICT outside of regular working hours.