Purpose: Electronic Patient Reported Outcomes (e-PRO) improves cancer patient quality of life and overall survival. Digital divide might lead to unequal access to telehealth. The aim of this study was to evaluate how a dedicated human and IT support program could bridge the digital divide. Methods: Between February 2021 and June 2022, solid cancer outpatients undergoing chemotherapy at the Mondor Teaching Hospital, France, were provided with the e-PRO Onco’nect® tool. Patients with digital disconnection were offered an IT and human dedicated program (lending of a tablet, caregivers, educational program, technical, peer-to-peer support). We collected data on patients’ healthcare pathways, and we performed semi-structured interviews to assess patients’ challenges.Results: We enrolled 22 patients: 15 females, 50% were aged > 70 years (interquartile range (IQR), 64–74), 14 had gastro-intestinal cancer, 15 patients had metastases, 14 lived alone. Ten patients out of 22 benefited from the program and completed > 50% of the questionnaires and 5/22 (23%) completed > 75%. The majority (12/22) remained poor adherent to e-PRO during a median treatment duration of 4 months (IQR, 3–7). There was no association between the level of social deprivation and the completeness of questionnaires. The underuse of the e-PRO went beyond patients’ understanding of its clinical relevance and their technical competence and was related to a poor health literacy and an emotional burden. Conclusion: IT and human support help a significant proportion of patients to access telehealth. Most of the disconnected patients were unable to engage digital health, mainly due to their health literacy level.