In a cooperative mixed-initiative system, timely and effective dialogue between the system and user is important to ensure that both sides work towards producing the most effective results, and this is affected by how disruptive any interruptions are as the user completes their primary task. A disruptive interaction means the user may become irritated with the system, or might take longer to deal with the interruption and provide information that the system needs to continue. Disruption is influenced both by the nature of the interaction and when it takes place in the context of the user’s progress through their main task. We describe an experiment based on a prototype cooperative video annotation system designed to explore the impact of interruptions, in the form of questions posed by the system that the user must address. Our findings demonstrate a preference towards questions presented in context with the content of the video, rather than at the natural opportunities presented by transitions in the video. This differs from previous research which concentrates on interruptions in the form of notifications.