Rather than studying workplace flexibility as the availability or usage of flexible work practices, in this study, we theorize workplace flexibility as a subjective psychological experience influenced by employees' perceptions of control over where and when they work (psychological job control) and control over their social boundaries (boundary control). Based on boundary and border theory, using a two-wave study conducted at an Italian bank (N = 1423) and adopting a person-centered approach through latent transition analysis (LTA), we identified four flexibility profiles characterized by different levels of psychological job control and boundary control, with the same structure, dispersion, and sizes over time. The four profiles were: (1) flexible non-dividers (3.46 %), marked by high psychological job control and low boundary control; (2) flexible dividers (34.83 %), characterized by high levels of both psychological job control and boundary control; (3) non-flexible dividers (50.74 %), featuring low psychological job control but high boundary control; and (4) non-flexible non-dividers (10.97 %), with low levels of both types of control. Three of these profiles exhibited high within-person stability across time, while the flexible non-dividers profile was highly unstable, with many members transitioning to profiles with higher boundary control at Time 2. Organizational investments in training and communication programs may have contributed to these transitions from low to high boundary control profiles. Gender and age emerged as significant predictors of profile membership, with gender effects shifting over time: at Time 1, men were more likely to be in non-flexible dividers profile, while at Time 2, they were more likely to be in the flexible non-dividers profile. Age effects also changed: older workers were more likely to be in the flexible non-dividers profile at Time 1 but shifted toward the flexible dividers profile by Time 2. Parental status was not significant, whereas carer status was significant only at Time 1, where being a carer increased the likelihood of employees belonging to the flexible dividers profile compared to the non-flexible dividers. Our findings further revealed that the psychological experience of work flexibility positively impacts wellbeing when employees experience control over both work and social boundaries. Flexible dividers consistently exhibited the highest levels of work engagement, job satisfaction, and work-life balance across both Time 1 and Time 2. In contrast, flexible non-dividers showed a significant decline in these outcomes over time. Profiles with low boundary control, especially flexible non-dividers and non-flexible non-dividers, reported the lowest levels of wellbeing. Despite some improvements in non-flexible non-dividers profile from Time 1 to Time 2, it remained to have the lowest scores on all outcomes, emphasizing the critical role of boundary control in maintaining employee wellbeing over time. These findings provide a possible explanation regarding the “autonomy-control paradox,” where flexibility in work location and timing may reduce autonomy unless social boundaries are effectively managed. Having control over one's social domains allows for the benefits of workplace flexibility and reduces the risk that flexibility in where and when to work undermines the autonomy it is meant to provide.