The digital revolution has completely changed the way that certain industries operate. In particular, there has been a huge transformation in the healthcare industry, since the wake of new technologies and digitization. Businesses are leveraging data to operate. Many healthcare organizations collect and store their patient data across their complex infrastructure (for example; cloud storage). Inadvertently stored sensitive data can be a threat to any organization. Especially, the recent outbreak of COVID-19 has become a profitable opportunity for cyber attackers to lure targets in the name of coronavirus and install malware to steal data. As many companies are now working remotely, the strength of data security is often going for a toss. Hence, every organization must understand the importance of introspecting its current security posture and close all the gaps and vulnerabilities from time to time. The case study describes how a health care giant faced challenges in enhancing their security posture. Then it narrates, how SISA’s Vulnerability Assessment and Penetration Testing (VAPT) team identified the gaps in the architecture and mitigated all the issues within no time. In addition, the case study lists the closure points suggested by SISA’s VAPT team and how mitigation measures helped the organization in building a robust security posture. The case study was researched and compiled by Anantha Krishna, VAPT Team Lead at SISA.