Recent research in IT adoption indicates that users do not always acknowledge the objective superiority of new technologies and stay with incumbent technologies for reasons like habits, inertia, overuse, or even addiction. The theoretical scope on the phenomena around hesitant switching behaviors or even resistance to switch, is often based on the explanatory approaches to the question of why individuals refuse to switch to apparently superior technologies and how switching can be assisted. The results of this research have succeeded in providing theoretical and empirical explanations to the question why individuals don’t take the step towards a new system, but they have not explained why individual users maybe intentionally and determinedly stay with incumbent technologies. With our study we turn the question and investigate what mechanism leads to the deliberate choice of an incumbent technology and overrules a cognitive evaluation of a technology. We turn to attachment theory and apply its theoretical foundation to our research objective. The findings of our data analysis suggest that technology attachment is a strong predictor of actual usage and provide the first evidence for the existence of technology attachment.