At Nylas, a shift from individual to collaborative debugging significantly improved the resolution of technical issues, as demonstrated through two case studies involving different bugs. The first bug, involving duplicate calendar events, remained unresolved for a long time due to insufficient information sharing and repeated efforts by multiple engineers working in isolation. The lack of collaboration led to missed opportunities, including the inability to access necessary logs within a critical two-week window. Conversely, the second bug, related to retrieving a raw MIME message, was effectively resolved through a collaborative approach that included gathering detailed user information, documenting each step of the investigation, and handing over progress efficiently between engineers. This process allowed for seamless continuity and ultimately led to a successful fix. The experience underscored the importance of treating debugging as a collective, long-term effort rather than solely a technical challenge, emphasizing the role of communication and process improvement in problem-solving.