Accredited Social Health Activist (ASHA) workers serve as indispensable connectors between healthcare systems and underserved communities, initiated under the National Rural Health Mission (NRHM) of the Government of India (GoI). ASHA ensures that the provision of essential health services is provided, and it promotes preventive action. Despite their extensive role, ASHA workers face considerable challenges, particularly related to the documentation process mandated by the ASHA diary. Therefore, the primary objective of this work is to investigate the usability issues in the ASHA diary, focusing on how these issues affect the efficiency and effectiveness of ASHA workers in maintaining and retrieving accurate patient records. The mixed-methods study involving 37 ASHA workers was conducted in the Jabalpur and Mirzapur districts of India. Data were collected and validated using Nielson’s heuristic principles, observations, and modified questionnaires. The study evaluated and confirmed several usability problems, including poor visibility of the system, inconsistent data entry formats, inadequate error prevention mechanisms, etc. This study highlights the need to redesign the ASHA diary from the user perspective to improve the management of healthcare data and deliver quality health care in rural areas. Resolving usability issues can significantly reduce ASHA workers’ stress and workload, thereby enhancing the quality of rural health services.