With respect to the tremendous deficit in surgical care plaguing developing nations, it is critical that medical outreach models be organized in such a fashion that sustainable advancements can be durably imparted beyond the duration of targeted missions. Using a didactic framework focused on empowering host neurosurgeons with an enhanced surgical skillset, a mission was launched in Managua, Nicaragua, after previous success in Kiev, Ukraine, and Lima, Peru. Unfortunately, the failure to critically assess the internal and external state of affairs of the region’s medical center compromised the outreach mission. Herein lies the visiting team’s lessons from failure and insights on facilitating effective communication with host institutions, circumventing geopolitical instability, and utilizing digital collaboration and video-conferencing tools in the post-COVID-19 era to advance the surgical care of developing regions in a fashion that can be generationally felt.