Noise is a persistent issue in indoor environments such as shared offices, where acoustic treatments may not provide sufficient auditory comfort. Sound masking systems, which reduce speech intelligibility by adding background noise, can be effective but typically increase overall sound levels, leading to very mixed results in the literature. This paper first presents an exploratory experiment that examines sound masking to enhance shared indoor soundscapes. The sound mixtures created using two ventilation noises and five water sounds are evaluated for their pleasantness. While variations in pleasantness are related to the type of water sound, the results raise some questions about what is perceived as annoying, what is considered pleasant, and what practical elements should be considered to improve sound comfort. To conduct more in-depth research about contextual elements, a forthcoming diary study is initiated to investigate people’s sound-related experiences, behaviors, and needs in shared offices. The methodology used to design this study is presented, as well as the expected results and perspectives, offering insights into auditory experiences at work and informing the development of audio augmented reality approaches.