This paper describes methodology and results from a model-based analysis of data on sound transmission from controlled sound sources at sea to a 10-km distant shore. The data consist of registrations of sound transmission loss together with concurrently collected atmospheric data at the source and receiver locations. The purpose of the analysis is to assess the accuracy of methods for transmission loss prediction in which detailed data on the local geography and atmospheric conditions are used for computation of the sound field. The results indicate that such sound propagation predictions are accurate and reproduce observed variations in the sound level as function of time in a realistic way. The results further illustrate that the atmospheric model must include a description of turbulence effects to ensure predicted noise levels to remain realistically high during periods of sound shadow.