The current research efforts in the security domain are essentially inspired by the intention to ensure both healthcare software's security and usability. Practitioners are continuously working on techniques that can optimise security while affording the ease of use. Inspite of the numerous efforts by the developers and security experts in this context, the level of usability-security is not the same as it should be. Furthermore, it is important to do more work on the most effective strategies for evaluating and increasing the usable-security of healthcare technology. Quantitative usability and security assessment is an important part of increasing the standards of software security especially with regard to software used in healthcare. This study's objective, in particular, is to evaluate the usability-security of healthcare software. Thereafter, based on the empirical analysis of comprehensive data, the study recommends the strategies that would facilitate in designing healthcare software with optimum safety while preserving its' usability. Decision makers often find it difficult to integrate highly secure software with maximum usability while developing the software. Hence, this research endeavour enlists the assimilation of usability and safety with their contributory attributes. Moreover, this study proposes the use of a novel technique of combining the Analytic Network Method (ANP), Fuzzy Sets (FS), and Technique for Order of Preference by Similarity to Ideal Solution (TOPSIS) to test usability together with security. The researchers employed the suggested methodology on six applications of the hospital management systems in Mecca, Saudi Arabia, to ascertain the utility of the FS-AHP-TOPSIS hybrid solution technique. Usability results along with security assessment corroborated that the most accurate and effective method for evaluating the usable-security of healthcare applications will be this innovative hybrid approach. Most relevantly, these findings will be useful in the security management without impacting the usability for the end users.