In a reflection on current cybersecurity challenges, David Jacoby, a seasoned white-hat hacker and co-founder of Sprinkler Security, highlights the evolving landscape of IT security, emphasizing the importance of integrating knowledge across various specialized interest groups like network segmentation and vulnerability management. With over 25 years in the field, Jacoby illustrates the persistent vulnerabilities in systems, including weak password practices and poor network segmentation, through real-life penetration tests. Despite advancements and increased collaboration between security researchers and companies, such as the expansion of the bug bounty community, Jacoby points out that organizations often overlook basic security measures, which can lead to significant breaches even without exploiting zero-day vulnerabilities. He underscores that protecting both external and internal networks is crucial, advocating for comprehensive strategies including system hardening and security awareness to mitigate risks posed by compromised devices and password reuse.