The healthcare and pharmaceutical sectors face significant cybersecurity challenges due to their sensitive data and critical systems, which are often compromised by outdated technology and limited resources. These industries are frequent targets for nation-state actors seeking to steal intellectual property, as well as cybercriminals deploying ransomware to disrupt hospital operations, exploiting the urgency to protect patient safety. Personal health information is highly valued on the black market, making it a frequent target for organized crime. Red team exercises in these sectors aim to test the resilience of healthcare operations and data protections, focusing on vulnerabilities in medical devices, patient portals, and pharmaceutical R&D data. The exercises highlight the importance of addressing legacy system vulnerabilities, emphasizing the need for improved network segmentation, multi-factor authentication, and timely patching of medical software. Demonstrating the potential for swift, undetected cyberattacks is crucial for securing budget approvals for enhanced defenses, as evidenced by simulated scenarios where attackers could severely impact patient care within a short time frame.