<b>Purpose:</b> This study aimed to explore the patient-dietitian experience during an 18-week nutrition counselling intervention delivered using the telephone and a mobile application to people newly diagnosed with upper gastrointestinal (UGI) cancer. <b>Methods:</b> Qualitative case study methodology was followed, whereby the case was the 18-week nutrition counselling intervention. Dietary counselling conversations and post-intervention interviews were inductively coded from six case participants which included fifty-one telephone conversations (17h), 244 written messages, and four interviews. <b>Results:</b> Themes describing the roles of the dietitian were as follows: regular collaborative problem-solving to encourage empowerment, a reassuring care navigator including anticipatory guidance, and rapport building via psychosocial support. Despite intensive counselling from the dietitian, nutrition impact symptom management was a core unmet need as it required intervention beyond the scope of practice for the dietitian. <b>Conclusion:</b> Delivery of nutrition care via the telephone or an asynchronous mobile application to people with newly diagnosed UGI cancer required the dietitian to adopt a range of roles to influence nutritional intake: they empower people, act as care navigators, and provide psychosocial support.