Facilitated by information and communication technologies (ICT), employees increasingly make switches between their work and home boundaries. These technology-facilitated boundary role transitions (TFT) can either occur at work—for instance, using your phone at work for private concerns—or at home—for instance, engaging in ICT use in the evening for work purposes. We examine whether TFT at work and at home reinforce each other via home-to-home conflict and work-to-work conflict. Drawing on boundary role theory, we hypothesize that TFT at work is positively related to home-to-work conflict, which in turn triggers TFT at home, resulting in increased work-to-home conflict that day and increased TFT at work the next day. We test our model at within- and between-person level using a sample of 241 Belgian employees who completed two daily surveys (i.e., a morning and an afternoon survey) during five consecutive working days (Ndatapoints = 756). Multilevel path analysis showed that employees who engaged more in TFT at work, experienced on average higher home-to-work conflict, which was related to more TFT at home and, consequentially, with higher work-to-home conflict in the evening. This points to a loss spiral of TFT and work-home conflict on a between-person level. On a within-person level, we found that TFT at work was related with more home-to-work conflict and TFT at home with more work-to-home conflict that day. Yet, contrary to our hypotheses, daily home-to-work conflict did not predict daily TFT at home and neither daily nor between-person work-to-home conflict predicted TFT at work the next day. Our findings are the first to show reinforcing but no time-lagged effects of TFT and work-home conflicts and show the risk of the use of ICT at work for private purposes for work-home conflicts. These results nuance the usefulness of TFT as an effective boundary work strategy.