Ensuring the effectiveness factor of usability consists in ensuring that the application allows users to reach their goals and perform their tasks. One of the few means for reaching this goal relies on task analysis and proving the compatibility between the interactive application and its task models. Synergistic execution enables the validation of a system against its task model by co-executing the system and the task model and comparing the behavior of the system against what is prescribed in the model. This allows a tester to explore scenarios in order to detect deviations between the two behaviors. Manual exploration of scenarios does not guarantee a good coverage of the analysis. To address this, we resort to model-based testing (MBT) techniques to automatically generate scenarios for automated synergistic execution. To achieve this, we generate, from the task model, scenarios to be co-executed over the task model and the system. During this generation step we explore the possibility of including considerations about user error in the analysis. The automation of the execution of the scenarios closes the process. We illustrate the approach with an example.