In order to understand the heat transfer performance, startup, and fluid flow conditions of oscillating heat pipes (OHPs) with a hydraulic diameter far exceeding the maximum hydraulic diameter (MHD) defined by , an experimental investigation on the OHP heat transfer performance and visualization was conducted. The effects of heat input, working fluid, and orientation on the oscillating motion and heat transfer performance of the investigated OHPs have been conducted. In addition, the detailed flow patterns of the tested OHPs were recorded by a high-speed camera from both vertical and horizontal orientations. Results show that the maximum hydraulic diameter, which can form a train of liquid plugs and vapor bubbles, which is essential for an OHP to function, depends on the heat input, working fluid, and orientation. At a power input of 1000 W, the OHP can still function well even when the tube diameter exceeds the MHD of 91.6%. This maximum hydraulic dimeter depends on the orientation. While the OHP with a dimeter far exceeding the MHD can still function, the heat transfer performance of the OHP in a vertical orientation is better than in a horizontal orientation.