Recent in vitro studies have shown that air pockets can get trapped at the coupling interface of the treatment head in dry-head lithotripsy, and this can pose a significant barrier to transmission of shock wave energy to the focal zone. Breakage of model stones is very sensitive to the presence of air pockets at the coupling interface. The quality of routine coupling is highly variable, and it seems quite feasible that the way in which the coupling gel is applied may have a significant effect on the quality of coupling. Therefore, attempts to find the best coupling regime may be valuable to perform, and preliminary results of in vitro tests are presented in this report. Experiments were conducted using gel or castor oil as coupling agents. The test tank was coupled through a transparent Mylar membrane to the water-filled cushion of the treatment head, so that pockets of air trapped between the two coupling surfaces could be observed and photographed. It is shown that the quality of coupling can be improved by applying an excessive amount of gel to just the water cushion of the lithotripter, while applying gel to both the water cushion and the Mylar membrane typically gives poor coupling. Repeat decoupling and recoupling substantially degraded the quality of coupling, reducing shock wave energy density at the target by ∼80%. It was also observed that using castor oil as a coupling medium does not guarantee air-free coupling.