The integration of digital technologies into measuring instruments (MI) poses new challenges for ensuring the reliability and security of software. This study presents a comprehensive approach to risk assessment when assessing the conformity of MI software. The proposed methodology goes beyond WELMEC 7.2, considering both technical vulnerabilities and operational risks in different application environments. A key aspect of the approach is the classification of risks into low and high categories, assigning conditional scores to facilitate structured decision-making. Given the potential consequences of software failures – from economic losses to security threats – the establishment of a robust risk management system is crucial. In the absence of statistical data, expert assessment methods are a viable alternative for assessing potential threats. The study also highlights the importance of harmonizing risk assessment practices across different regulatory environments. While OIML D 31 and MID 2014/32/EU lay the foundation, national regulations introduce additional complexity. The automation of the proposed approach simplifies the software compliance assessment procedure. By integrating international standards with innovative risk assessment methodologies, this study enhances the reliability, security, and compliance of MI software.