In today's digital era, even robust security frameworks like OWASP and MITRE ATT&CK can prove inadequate against sophisticated phishing attacks. These attacks leverage official chat functionalities in web and mobile applications, causing significant disruptions within the tourism and lodging sectors of modern web applications. This presentation unveils a series of firsthand encounters with such attacks, illustrating their impact and tracing them back to a major cybercriminal ecosystem that utilizes Telegram bots. Through meticulous research and open-source threat intelligence, the discussion explores the vulnerabilities and shortcomings major organizations face in defending against these threats. Key lessons in secure coding, detection engineering, proactive threat intelligence, and security awareness are highlighted, providing attendees with insights to fortify their defenses with a multi-layered security approach. This approach aims to mitigate evolving cyber risks and protect both web applications and brand integrity.