In nowadays, individuals should do their unpaid labors in the form of self-service, which is so called by involuntary digital shadow work, even though they have enjoyed automated and intelligent digital services due to the advancement of digital technologies such as artificial intelligence and big data. In order to explore the essentials of such unique behaviors, we have aimed to identify individuals’ psychological mechanism which governs involuntary digital shadow work. By using the grounded theory methodology, we have conducted in-depth interviews with 12 individuals who have prior experiences on doing involuntary digital shadow work such as changing passwords, updating applications and deleting spam-mails. By analyzing the interview manuscripts, we have extracted 69 concepts in the coding steps and ultimately developed 6 key categories by either comparing or incorporating similar concepts from the initial concepts. In this grounded theory-based study, we found that there are two types of decision making such as decision making for formulating shadow work intention and decision choices for completing the shadow work during the interactions between human and digital technologies as trigger of initiating shadow work. This study has also found that there are two types of unique attitudes during the digital shadow environments such as negative attitude when performing shadow and attitude toward the phenomenon that occurs when individuals do not do shadow work. Finally, we have presented three types of psychologically controllable drivers such as the degree of adherence to individuals’ own unique digital technology management approach, the degree of cognitive effort required for shadow work, the degree of individuals’ perception of what to do for either facilitating or inhibiting individuals’ shadow work. The implications of our findings for both theory and practice are discussed.