The increasing frequency of cyber threats has underlined the need for robust security measures in IT infrastructures, particularly within the healthcare sector. This paper explores the role of penetration testing in identifying vulnerabilities and assessing the impact of various security testing techniques—automated, hybrid, and manual—on a virtualized healthcare network. Through simulated attack scenarios, we analyze network behavior under vulnerability conditions, evaluating factors such as performance, resource consumption, and anomaly detection. Additionally, we investigate the broader landscape of cybersecurity threats targeting healthcare, referencing ENISA reports that rank healthcare among the top sectors affected by cyberattacks, particularly ransomware, DDoS attacks, and data leaks. By correlating these threats with security vulnerabilities in eHealth applications, we aim to provide insights into the need for robust cybersecurity measures. Finally, our study examines digital artifacts essential for cybersecurity investigations and their role in identifying attack vectors and system weaknesses. The conclusions drawn from our research emphasize the necessity of proactive security strategies, incident response measures, and regulatory compliance to protect healthcare infrastructures against evolving cyber threats.