Introduction: Greenland has one of the highest prevalences of otitis media in the world. However, access to ear specialists throughout Greenland is limited and currently there are no national guidelines for treatment or prevention. Tele-otoscopy may be beneficial in optimizing diagnosis and treatment. The smartphone otoscopy device, Cupris®, has previously been validated when used by medical doctors on a population primarily consisting of adults. In this study we evaluated the usability of the Cupris® otoscope when used by local health care workers with different levels of training and education, examining children aged 1–6 years. Methods: We conducted a cross-sectional study in three Greenlandic towns. Health care personnel were asked to perform video-otoscopy on children contacting the health clinic for any reason. The videos were sent for remote evaluation by three ear specialists who rated the videos on a five-point Likert scale and provided information on challenges with the videos. The dichotomous outcome “not useful/useful” was defined as 1–3 and 4–5 on the Likert scale, respectively. Results: In total, 142 videos were recorded on 84 patients. Mean proportion of useful videos was 18.1%, with a modified Fleiss’ Kappa interrater agreement coefficient of 0.67 95% CI [0.57–0.76] corresponding to substantial agreement among the three raters. Conclusions: In this study the usefulness of the Cupris® TYM otoscope did not prove to be sufficient with the presented instruction in the hands of local health care workers when examining Greenlandic children. Focus on training and education of local health personnel is crucial and warranted before advantageous implementation for non-specialist health care workers can be expected.