Hearing aids can be effective devices to compensate for age- or non-age-related hearing losses. Their overall adoption in the affected population is still low, especially in underdeveloped countries in the subpopulation experiencing milder hearing loss. One of the major reasons for low adoption is the need for repeated complex fitting by professional audiologists, which is often not completed for various reasons. As a result, self-fitting procedures have been appearing as an alternative. Key open questions with these digital tools are linked to their effectiveness, utilized algorithms, and achievable end-results. A digital self-fitting prototype tool with a novel quick four-step fitting workflow was evaluated in a study on 19 individuals with moderate hearing loss. The tool was evaluated in a double-blinded, randomized study, having two study aims: comparing traditional audiological fitting with the new self-fitting tool, which can also be used as a remote tool. The main reported results show moderately high usability and user satisfaction obtained during self-fitting, and quasi-equivalence of the performance of the classical audiological fitting approach. The digital self-fitting tool enables multiple sessions and easy re-fitting, with the potential to outperform the classical fitting approach.