Enterprise information systems (IS) are systems that integrate and streamline business processes that involve volumes of data. They also assist managers in making better decisions across organizations. In these ISs an upstream action has a bullwhip effect on downstream activities. The knowledge required to conduct operations with IS includes system interface navigation and tacit business processes. Although short-term training has been an essential part of implementing IS, it has been difficult to convey the cross-functional process knowledge required to operate an IS when errors occur. On the other hand, mentoring has long been employed by organizations to transfer and propagate tacit knowledge. Notwithstanding that no research has been done on the impact of mentoring on IS successful adaptation, the present study examines the mentoring theory used in successful organization and IS success models in a second-order modelling to argue, and verify, that mentoring plays an important role in IS adaptation through users’ perceived usefulness, satisfaction, and continuous intention.