Research into human performance on naval ships often emphasizes the significance of shaping factors, such as vigilance, fatigue and circadian rhythm. However, few report on the presence of complex nonlinear dynamics and fractal dimensionality. This study examines over 7000 routine topside security checks on a U.S. Navy Destroyer performed over a twelve-month period. Time series analysis (0-1 test, analysis of Lyapunov exponent, state space plots, and graphical analysis) reveal the presence of chaotic behavior, harmonics attractors, and fractal structures. The presence of this level of complexity in a simple task demonstrates the need to integrate previous findings in human performance with new discoveries in complexity and fractional dynamics.