The traditional method of software robustness evaluation, through error injection, is for errors to be injected at reaching a specific code location. This paper studies what impact varying the time for error injection has on evaluation of software (specifically Operating Systems (OS)) robustness. A strategy to guide the appropriate error injection timing is proposed, based on the observation that the operational usage profile of a driver shows a high degree of regularity in the calls being made. Using the concept of call blocks (i.e., a distinct sequence of calls made to the driver), the trigger for injection can be used to guide injections into different system states, corresponding to the operations carried out. A real-world case study compares the effectiveness of the proposed strategy to a traditional location-based approach, and shows that significantly more useful insights can be gained using the proposed approach.