This study sought to highlight tutors' voices and experiences using reflective practices and purposeful exploration to illustrate their complex and transformational journey transitioning into the online environment. This interpretive phenomenological analysis offered a deeper and richer exploration of the intricacies of five tutors' experiences by discovering what it meant to shift from campus-based settings into the online environment and the ways tutoring roles, practices, and communication, among other aspects, were influenced in the transition process. This study also examined whether the tutors' experiences aligned with aspects of Herring's (2019) Multimodal Communication theory and Yellin's (1999) Role Acquisition theory. The study found that when shifting online, tutors remained in a constant state of transition, whether it was months or years after their first online writing tutoring session. Before the start of their online tutoring experience, the participants reported that their experiences began with a sense of loss, distress, and negativity or reserve regarding the online environment. However, after their initial online tutoring sessions, they gained relief. Through continued online tutoring sessions, the participants faced challenges that required adjustments and changes to overcome. Eventually, the mere experience of tutoring online led to a transformational mindset, as the participants began viewing the online environment positively. The study partially confirmed Herring and Yellin's respective theories and discovered that computer-mediated communication may influence the roles tutors play. The study also found that tutors experience more fluid roles in the online environment compared to campus-based settings. The participants acknowledged that they never fully transitioned online and were in a constant state of flux. The findings of this study have implications for learning and writing centers, as spaces that intersect campus and online writing support as well as the potential to reimagine online tutoring roles, policies, strategies, and integrated support. Recommendations for future research were also documented. Overall, the study revealed that the online environment is complex and required changes in roles, strategies, and self for tutors to gain comfort, confidence, and positivity, as they continued to reside in a state of transition. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]