Shell Exploration & Production Company is working with academic, non-profit, and federal stakeholders in the Gulf of Mexico to develop and implement long term environmental offshore monitoring programs. One such program, started in 2008 between Shell and the National Oceanic and Atmospheric Administration, has expanded to include new collaborators working together to operate multiple underwater gliders for monitoring the physical environment. In this paper, we summarize Loop Current dynamics and glider observations during the 2016 season, highlight lessons learned since the start of the glider program in 2012, and introduce a new deep ocean observing component to this collaboration.