This is an investigation into the feasibility of agentprovided assistance for two specific situations, (1) when a previously-interrupted task is resumed, offer to open previously-used contextual documents and (2) when a non-optimal task is begun, suggest a more suitable alternative task. A paper-based task places participants in the situations described. The concern is to maximise the balance between helpfulness and annoyance. The results are discussed in terms of timing of interruption and social effects. Overall, the agent needs to take account of the human’s likely feelings towards any intervention and not assume that it is correct, even when it is.